Addition Of Chiral And Achiral Allyltrichlorostannanes To Chiral α-alkoxy Aldehydes

Achiral and chiral allyltrichlorostannanes reacted with chiral α-alkoxy aldehydes to give the corresponding homoallylic alcohols with moderate to good levels of 1,4-syn-diastereoselection.204802812Fleming, I., Barbero, A., Walter, D., (1997) Chem. Rev., 97, p. 2063Nishigaichi, Y., Takuwa, A., Naruta, Y., Maruyama, K., (1993) Tetrahedron, 49, p. 7395Panek, J.S., Xu, F., Rondon, A.C., (1998) J. Am. Chem. Soc., 120, p. 4113Zhu, B., Panek, J.S., (2001) Eur. J. Org. Chem., 9, p. 1701Huang, H.B., Spande, T.F., Panek, J.S., (2003) J. Am. Chem. Soc., 125, p. 626Keck, G.E., Abbott, D.E., (1984) Tetrahedron Lett, 25, p. 1883Maguire, R.J., Mulzer, J., Bats, J.W., (1996) J. Org. Chem., 61, p. 6936Denmark, S.E., Stavenger, R.A., (1998) J. Org. Chem., 63, p. 9524Trost, B.M., Urabe, H., (1990) J. Org. Chem., 55, p. 3982Nishigaishi, Y., Takuwa, A., Jodai, A., (1991) Tetrahedron Lett, 32, p. 2383Almendros, P., Gruttadauria, M., Helliwell, M., Thomas, E.J., (1997) J. Chem. Soc. Perkin Trans. I, p. 2549Deka, D.C., Helliwell, M., Thomas, E.J., (2001) Tetrahedron, 57, p. 10017Martin, N., Thomas, E.J., (2001) Tetrahedron Lett, 42, p. 8373Kumar, P., Thomas, E.J., Tray, D.R., (2001) J. Braz. Chem. Soc., 12, p. 623Gruttadauria, M., Thomas, E.J., (1995) J. Chem. Soc. Perkin Trans. I, p. 1469Nishigaichi, Y., Kuramoto, H., Takuwa, A., (1995) Tetrahedron Lett, 36, p. 3353Dias, L.C., Giacomini, R., (1998) J. Braz. Chem. Soc., 9, p. 357Dias, L.C., Giacomini, R., (1998) Tetrahedron Lett, 39, p. 5343Dias, L.C., Meira, P.R.R., Ferreira, E., Org. Lett., 1999, p. 1335. , See also: "NMR Spectra and Structures of Organotin Compounds," V. S. Petrosyan, Progr. in NMR Spectr. 1978, 11, 115Dias, L.C., Meira, P.R.R., (2000) Synlett, p. 37Dias, L.C., Ferreira, E., (2001) Tetrahedron Lett, 42, p. 7159Dias, L.C., Ferreira, A.A., Diaz, G., (2002) Synlett, p. 1845Dias, L.C., Diaz, G., Ferreira, A.A., Meira, P.R.R., Ferreira, E., (2003) Synthesis, p. 603Dias, L.C., Giacomini, R., Meira, P.R.R., Ferreira, E., Ferreira, A.A., Diaz, G., dos Santos, D.R., Steil, L.J., (2003) Arkivoc, 10, p. 240Dias, L.C., dos Santos, D.R., Steil, L.J., (2003) Tetrahedron Lett, 44, p. 6861(2002) Org. Lett., 4, p. 4325. , We have recently described a very efficient, synthetically useful 1, 4-anti-1, 5-anti boron-mediated aldol reaction of chiral α-methyl-β-alkoxy methyl ketone with achiral aldehydes: Dias, L.C., Baú, R.Z., de Sousa, M.A., Zukerman-Schpector, JDenmark, S.E., Wilson, T., Willson, T.M., (1988) J. Am. Chem. Soc., 110, p. 984Denmark, S.E., Weber, E.J., Wilson, T., Willson, T.M., (1989) Tetrahedron, 45, p. 1053Denmark, S.E., Almstead, N.G., (1992) Tetrahedron, 48, p. 5565Denmark, S.E., Almstead, N.G., (1993) J. Am. Chem. Soc., 115, p. 3133Dias, L.C., Fattori, J., Perez, C.C., (2008) Tetrahedron Lett, 49, p. 557Dias, L.C., Fattori, J., Perez, C.C., Oliveira, V.M., Aguilar, A.M., (2008) Tetrahedron, 64, p. 5891Kim, D., Lee, J., Shim, P.J., Lim, J.I., Doi, T., Kim, S., (2002) J. Org. Chem., 67, p. 772noteShambayati, S., Schreiber, S.L., Blake, J.F., Wierschke, S.G., Jorgensen, W.L., (1990) J. Am. Chem. Soc., 112, p. 697noteChérest, M., Felkin, H., Prudent, N., (1968) Tetrahedron Lett, 18, p. 2199Anh, N.T., Eisenstein, O., (1977) Nouv. J. Chem., 1, p. 61noteBatey, R.A., Thadani, A.N., Smil, D.V., Lough, A.J., (2000) Synthesis, 7, p. 990Heathcock, C.H., Pirrung, M.C., Sohn, J.E., (1979) J. Org. Chem., 44, p. 4294Landmann, B., Hoffmann, R.W., (1987) Chem. Ber., 120, p. 331Dias, L.C., Ferreira, M.A.B., Tormena, C.F., (2008) J. Phys. Chem. A, 112, p. 232Sames, D., Liu, Y., De Young, L., Polt, R., (1995) J. Org. Chem., 60, p. 2153Lombardo, M., Morganti, S., Trombini, C., (2003) J. Org. Chem., 68, p. 997notenotenot

A Short Approach To Trisubstituted γ-butyrolactones

The dihydroxylation of unsaturated aldol adducts with catalytic OsO 4 and NMO occurs under very mild conditions and with moderate to excellent levels of diastereoselectivity to give trisubstituted γ-butyrolactone derivatives. © 2005 Elsevier Ltd. All rights reserved.472213216Maier, M.S., Marimon, D.I.G., Stortz, C.A., Adler, M.T., (1999) J. Nat. Prod., 62, p. 1565Lee, S.-C., Brown, G.D., (1998) J. Nat. Prod., 61, p. 29Chen, S.-Y., Joullié, M.M., (1984) J. Org. Chem., 49, p. 2168Brown, H.C., Kulkarni, S.V., Racherla, U.S., (1994) J. Org. Chem., 59, p. 365Schmitz, W.D., Messerschmidt, N.B., Romo, D., (1998) J. Org. Chem., 63, p. 2058Peng, Z.-H., Woerpel, K.A., (2001) Org. Lett., 3, p. 675Tobisu, M., Chatani, N., Asaumi, T., Amako, K., Ie, Y., Fukumoto, Y., Murai, S., (2000) J. Am. Chem. Soc., 122, p. 12663Fernandez, A.-M., Plaquevent, J.-C., Duhamel, L., (1997) J. Org. Chem., 62, p. 4007Trost, B.M., Rhee, Y.H., (1999) J. Am. Chem. Soc., 121, p. 11680Cahiez, G., Métais, E., (1997) Tetrahedron: Asymmetry, 8, p. 1373Miyabe, H., Fujii, K., Goto, T., Naito, T., (2000) Org. Lett., 2, p. 4071Fukuzawa, S., Seki, K., Tatsuzawa, M., Mutoh, K., (1997) J. Am. Chem. Soc., 119, p. 1482Martín, T., Martín, V.S., (2000) Tetrahedron Lett., 41, p. 2503Zhang, Q., Lu, X., (2000) J. Am. Chem. Soc., 122, p. 7604Sibi, M.P., Lu, J., Talbacka, C.L., (1996) J. Org. Chem., 61, p. 7848Forster, A., Fitremann, J., Renaud, P., (1998) Tetrahedron Lett., 39, p. 7097Chen, M.-J., Lo, C.-Y., Chin, C.-C., Liu, R.-S., (2000) J. Org. Chem., 65, p. 6362Lin, Y.-L., Cheng, M.-H., Chen, W.-C., Peng, S.-M., Wang, S.-L., Kuo, H., Liu, R.-S., (2001) J. Org. Chem., 66, p. 1781Shimada, S., Hashimoto, Y., Saigo, K., (1993) J. Org. Chem., 58, p. 5226Nagao, Y., Dai, W.-M., Ochiai, M., Shiro, M., (1989) J. Org. Chem., 54, p. 5211Nakamura, E., Oshino, H., Kuwajima, I., (1986) J. Am. Chem. Soc., 108, p. 3745Hannesian, S., Cooke, N.G., Dehoff, B., Sakito, Y., (1990) J. Am. Chem. Soc., 112, p. 5276Mandal, A.K., Mahajan, S.W., (1991) Synthesis, p. 311Chan, P.C.-M., Chong, J.M., (1990) Tetrahedron Lett., 31, p. 1981Ohkuma, T., Kitamura, M., Noyori, R., (1990) Tetrahedron Lett., 31, p. 5509Sibi, M.P., Deshpande, P.K., La Loggia, A.J., (1996) Synlett, p. 343Cho, K.W., Lee, H.-S., Rho, J.-R., Kim, T.S., Mo, S.J., Shin, J., (2001) J. Nat. Prod., 64, p. 664Takahata, H., Uchida, Y., Momose, T., (1994) J. Org. Chem., 59, p. 7201Pearson, A.J., Mesaros, E.F., (2002) Org. Lett., 4, p. 2001Yi, J., Luo, Y., Li, B., Zhang, G., (2004) Steroids, 69, p. 809Pinto, A.C., Freitas, C.B.L., Dias, A.G., Pereira, V.L.P., Tinant, B., Declercq, J.-P., Costa, P.R.R., (2002) Tetrahedron: Asymmetry, 13, p. 1025Costa, J.S., Dias, A.G., Anholeto, A.L., Monteiro, M.D., Patrocínio, V.L., Costa, P.R.R., (1997) J. Org. Chem., 62, p. 4002Barros, M.T., Maycock, C.D., Ventura, M.R., (2003) Org. Lett., 5, p. 4097Amador, M., Ariza, X., Garcia, G., Ortiz, J., (2004) J. Org. Chem., 69, p. 8172Chenevert, R., Rose, Y.S., (1998) Tetrahedron: Asymmetry, 9, p. 2827Gage, J.R., Evans, D.A., (1989) Org. Synth., 68, p. 83Evans, D.A., Bartroli, J., Shih, T.L., (1981) J. Am. Chem. Soc., 103, p. 2127Evans, D.A., Taber, T.R., (1980) Tetrahedron Lett., 21, p. 4675Evans, D.A., Ng, H.P., Clark, J.S., Rieger, D.L., (1992) Tetrahedron, 48, p. 2127Jaime, C., Segura, C., Dinarés, I., Font, J., (1993) J. Org. Chem., 58, p. 154Dinarés, I., Entrena, A., Jaime, C., Segura, C., Font, J., (1997) Electron. J. Theor. Chem., 2, p. 160notenot

Concerning The Application Of The1h Nmr Abx Analysis For Assignment Of Stereochemistry To Aldols Deriving From Aldehydes Lacking β-branches

Attempts to apply the 1H NMR ABX method for assignment of stereochemistry of β-hydroxy ketones to aldols 4-10 deriving from α-methyl aldehydes lacking β-branches reveals that the presence of a β-branch in the aldehyde reaction partner is necessary so that the average chemical environment of Ha and Hb is different for the Felkin and anti-Felkin aldols (see conformational pairs A/B and C/D, respectively). When the chiral α-methyl aldehyde lacks a β-branch, as in the case of the aldehyde precursors to 4-10, the conformational energies of E and F (for the Felkin β-hydroxy ketone derivatives), and conformers G and H for the anti-Felkin aldols, are too close in energy (within each pair), such that the average chemical and magnetic environments of Ha and Hb in the two diastereomers cannot be easily distinguished. This analysis provides a rational basis for application of the 1H NMR ABX pattern analysis to other β-hydroxy ketone derivatives. © 2005 American Chemical Society.70251046110465Dias, L.C., Baú, R.Z., De Sousa, M.A., Zuckerman-Schpector, J., (2002) Org. Lett., 4, p. 4325Liu, C.M., Smith III, W.J., Gustin, D.J., Roush, W.R., (2005) J. Am. Chem. Soc., 127, p. 5770Cowden, C.J., Paterson, I., (1997) Org. React., 51, p. 1Franklin, A.S., Paterson, I., (1994) Contemp. Org. Synth., 1, p. 317Heathcock, C.H., (1991) Comprehensive Organic Synthesis, 2, p. 181. , Heathcock, C. H., Ed.Pergamon Press: New YorkKim, E.M., Williams, S.F., Masamune, S., (1991) Comprehensive Organic Synthesis, 2, p. 239. , Heathcock, C. H., Ed.Pergamon Press: New YorkPaterson, I., (1991) Comprehensive Organic Synthesis, 2, p. 301. , Heathcock, C. H., Ed.Pergamon Press: New YorkBraun, M., (1987) Angew. Chem., Int. Ed. Engl., 26, p. 24Heathcock, C.H., (1984) Asymmetric Synth., 3, p. 111Evans, D.A., Nelson, J.V., Taber, T.R., (1982) Top. Stereochem., 13, p. 1Paterson, I., Goodman, J.M., (1989) Tetrahedron Lett., 30, p. 997Paterson, I., Florence, G.J., (2000) Tetrahedron Lett., 41, p. 6935Evans, D.A., Coleman, P.J., Côté, B., (1997) J. Org. Chem., 62, p. 788Evans, D.A., Trotter, B.W., Coleman, P.J., Côté, B., Dias, L.C., Rajapakse, H.A., Tyler, A.N., (1999) Tetrahedron, 29, p. 8671Paterson, I., Collett, L.A., (2001) Tetrahedron Lett., 42, p. 1187Paterson, I., Gibson, K.R., Oballa, R.M., (1996) Tetrahedron Lett., 37, p. 8585Tanimoto, N., Gerritz, S.W., Sawabe, A., Noda, T., Filla, S.A., Masamune, S., (1994) Angew Chem., Int. Ed. Engl., 33, p. 673Roush, W.R., Bannister, T.D., Wendt, M.D., Jablonowski, J.A., Scheidt, K.A., (2002) J. Org. Chem., 67, p. 4275Arefolov, A., Panek, J.S., (2002) Org. Lett., 4, p. 2397Roush, W.R., Bannister, T.D., Wendt, M.D., Vannieuwenhze, M.S., Gustin, D.J., Dilley, G.J., Lane, G.C., Smith III, W.J., (2002) J. Org. Chem., 67, p. 4284Oikawa, Y., Yoshioka, T., Yonemitsu, O., (1982) Tetrahedron Lett., 23, p. 889noteHeathcock, C.H., Pirrung, M., Sohn, J.E., (1979) J. Org. Chem., 44, p. 4294not

High 1,4-syn-induction In The Addition Of Chiral Allyltrichlorostannanestochiral Aldehydes

Chiral and achiral allyltrichlorostannanes reacted with chiral aldehydes to give the corresponding homoallylic alcohols with good to high diastereoselectivities. This approach has been applied to the synthesis of hydroxyethylene dipeptide isosteres L-682, 679, L-684,414, L-685,434 and L-685,458.200310240261Fleming, I., Barbero, A., Walter, D., (1997) Chem. Rev., 97, p. 2063Nishigaichi, Y., Takuwa, A., Naruta, Y., Maruyama, K., (1993) Tetrahedron, 49, p. 7395Panek, J.S., Xu, F., Rondon, A.C., (1998) J. Am. Chem. Soc., 120, p. 4113Zhu, B., Panek, J.S., (2001) Eur. J. Org. Chem., 9, p. 1701Huang, H.B., Spande, T.F., Panek, J.S., (2003) J. Am. Chem. Soc., 125, p. 626Keck, G.E., Abbott, D.E., (1984) Tetrahedron Lett., 25, p. 1883Trost, B.M., Urabe, H., (1990) J. Org. Chem., 55, p. 3982Nishigaishi, Y., Takuwa, A., Jodai, A., (1991) Tetrahedron Lett., 32, p. 2383Almendros, P., Gruttadauria, M., Helliwell, M., Thomas, E.J., (1997) J. Chem. Soc. Perkin Trans. 1, p. 2549Deka, D.C., Helliwell, M., Thomas, E.J., (2001) Tetrahedron, 57, p. 10017Martin, N., Thomas, E.J., (2001) Tetrahedron Lett., 42, p. 8373Kumar, P., Thomas, E.J., Tray, D.R., (2001) J. Braz. Chem. Soc., 12, p. 623Evans, D.A., Coleman, P.J., Dias, L.C., (1997) Angew. Chem. Int. Ed. Engl., 36, p. 2738Evans, D.A., Trotter, B.W., Cote, B., Coleman, P.J., Dias, L.C., Tyler, A.N., (1997) Angew. Chem. Int. Ed. Engl., 36, p. 2744Dias, L.C., Meira, P.R.R., Ferreira, E., (1999) Org. Lett., 1, p. 1335Almendras, P., Gruttadauria, M., Helliwell, M., Thomas, E.J., (1997) J. Chem. Soc. Perkin Trans. 1, p. 2549Almendras, P., Thomas, E.J., (1997) J. Chem. Soc. Perkin Trans. 1, p. 2561Thomas, E.J., (1997) Chem. Commun., p. 411Keck, G.E., Abbot, D.E., (1984) Tetrahedron Lett., 25, p. 1883Keck, G.E., Castellino, S., (1986) J. Am. Chem. Soc., 108, p. 3847Keck, G.E., Castellino, S., Andrus, M.B., (1989) Selectivities in Lewis Acid Promoted Reactions, 289. , D. Schinzer, Ed.NATO ASI Series CKluwer Academic: Dordrecht, Chapter 5Yamamoto, Y., Maeda, N., Maruyama, K., (1983) J. Chem. Soc. Chem. Commun., p. 742Denmark, S.E., Wilson, T., Willson, T.M., (1988) J. Am. Chem. Soc., 110, p. 984Denmark, S.E., Weber, E.J., Wilson, T., Willson, T.M., (1989) Tetrahedron, 45, p. 1053Denmark, S.E., Almstead, N.G., (1992) Tetrahedron, 48, p. 5565Denmark, S.E., Almstead, N.G., (1993) J. Am. Chem. Soc., 115, p. 3133Dias, L.C., Giacomini, R., (1998) J. Braz. Chem. Soc., 9, p. 357Dias, L.C., Giacomini, R., (1998) Tetrahedron Lett., 39, p. 5343Chérest, M., Felkin, H., Prudent, N., (1968) Tetrahedron Lett., 18, p. 2199Anh, N.T., Eisenstein, O., (1977) Nouv. J. Chem., 1, p. 61noteDias, L.C., Dos Santos, D.R., Steil, L.J., (2003) Tetrahedron Lett., 44, pp. 6861-6866Gage, J.R., Evans, D.A., (1990) Org. Synth., 68, p. 83Evans, D.A., Bartroli, J., Shih, T.L., (1981) J. Am. Chem. Soc., 103, p. 2127Evans, D.A., Taber, T.R., (1980) Tetrahedron Lett., 21, p. 4675Evans, D.A., Downey, C.W., Shaw, J.T., Tedrow, J.S., (2002) Org. Lett., 4, p. 1127Evans, D.A., Dart, M.J., Duffy, J.L., Yang, M.G., (1996) J. Am. Chem. Soc., 118, p. 4322Dias, L.C., Baú, R.Z., De Sousa, M.A., Zukerman-Schpector, J., (2002) Org. Lett., 4, p. 4325Vacca, J.P., Condra, J.H., (1997) Drug Discov. Today, 2, pp. 261-272Steele, F.R., (1996) Nature Med., 2, pp. 257-258Huff, J.R., (1991) J. Med. Chem., 34, pp. 2305-2314Prasad, J.V.N.V., Rich, D.H., (1990) Tetrahedron Lett., 31, pp. 1803-1806Tomasselli, A.G., Heinrikson, R.L., (2000) Biochim. Biophys. Acta, pp. 189-214Garg, R., Gupta, S.P., Gao, H., Babu, M.S., Debnath, A.K., Hansch, C., (1999) Chem. Rev., 99, p. 3525Litera, J., Budesinsky, M., Urban, J., Soucek, M., (1998) Collect. Czech. Chem. Commun., 63, p. 231Litera, J., Weber, J., Krizova, I., Pichova, I., Konvalinka, J., Fusek, M., Soucek, M., (1998) Collect. Czech. Chem. Commun., 63, p. 541Evans, B.E., Rittle, K.E., Homnick, C.F., Springer, J.P., Hirshfield, J., Veber, D.F., (1985) J. Org. Chem., 50, p. 4615Dias, L.C., Meira, P.R.R., (2000) Synlett, p. 37Dias, L.C., Ferreira, E., (2001) Tetrahedron Lett., 42, p. 7159Gryko, D., Chalko, J., Jurczak, J., (2003) Chirality, 15, p. 514Bergmeier, S.C., (2000) Tetrahedron, 56, p. 2561Nájera, C., (2002) Synlett, p. 1388Benedetti, F., Miertus, S., Norbedo, S., Tossi, A., Zlatoidzky, P., (1997) J. Org. Chem., 62, p. 9348De Clercq, E., (2001) Pure Appl. Chem., 73, p. 55Shearman, M.S., Beher, D., Clarke, E.E., Lewis, H.D., Harrison, T., Hunt, P., Nadin, A., Castro, J.L., (2000) Biochemistry, 39, p. 8698Nadin, A., López, J.M.S., Neduvelil, J.G., Thomas, S.R., (2001) Tetrahedron, 57, pp. 1861-1864Dias, L.C., Ferreira, A.A., Diaz, G., (2002) Synlett, p. 1845Dias, L.C., Diaz, G., Ferreira, A.A., Meira, P.R.R., Ferreira, E., (2003) Synthesis, 4, p. 603not