Boogers, Jeroen A.F.

Feringa, Bernard

Minnaard, Adriaan J.

Peña, Diego

Vries, André H.M. de

Vries, Johannes G. de

English

The combination of monodentate ligands in the rhodium-catalysed enantioselective hydrogenation enables a new approach when searching for the optimal activity and enantioselectivity in catalysis.</p

Dissertations of the University of Groningen

   University of GroningenImproving conversion and enantioselectivity in hydrogenation by combining differentmonodentate phosphoramidites; a new combinatorial approach in asymmetric catalysisPeña, Diego; Minnaard, Adriaan J.; Boogers, Jeroen A.F.; Vries, André H.M. de; Vries,Johannes G. de; Feringa, BernardPublished in:Organic & Biomolecular ChemistryDOI:10.1039/ b302097eIMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite fromit. Please check the document version below.Document VersionPublisher's PDF, also known as Version of recordPublication date:2003Link to publication in University of Groningen/UMCG research databaseCitation for published version (APA):Peña, D., Minnaard, A. J., Boogers, J. A. F., Vries, A. H. M. D., Vries, J. G. D., & Feringa, B. (2003).Improving conversion and enantioselectivity in hydrogenation by combining different monodentatephosphoramidites; a new combinatorial approach in asymmetric catalysis. Organic & BiomolecularChemistry, 1(7), 1087-1089. https://doi.org/10.1039/ b302097eCopyrightOther than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of theauthor(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons).The publication may also be distributed here under the terms of Article 25fa of the Dutch Copyright Act, indicated by the “Taverne” license.More information can be found on the University of Groningen website: https://www.rug.nl/library/open-access/self-archiving-pure/taverne-amendment.Take-down policyIf you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediatelyand investigate your claim.Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons thenumber of authors shown on this cover page is limited to 10 maximum.Supplementary dataDiego Peña,a Adriaan J. Minnaard,*a Jeroen A. F. Boogers,b André H. M. de Vries,b Johannes G. de Vriesaband Ben L. Feringa*aa Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen,Nijenborgh 4, 9747 AG Groningen, The Netherlands.Fax: (+31) 50-3634296; Tel: (+31) 50-3634278; E-mail: b.l.feringa@chem.rug.nlb DSM Research-Life Sciences, Advanced Synthesis & Catalysis, P.O. Box 18, 6160 MD Geleen, The Netherlands.µ µβOOP NR1OOP NHPh OOP NR2R2R3R3(S)-1, R1 = Me, R2 = R3 = H(S)-4, R1 = R2 = Me, R3 = H(S)-5, R1 = Me, R2 = H, R3 = Br(S)-6, R1 = Bn, R2 = R3 = H(S,R)-2 (S)-3RCO2EtNHAc H2 (10 bar)Rh(COD)2BF4ligand RCO2EtNHAc7, R = Me8, R = Ph9, R = Me10, R = Phβµµ µµSupplementary dataentry substrate solvent L1 L2 conv (%) ee (%)1 7 i-PrOH 1 1 60 39.42 7 i-PrOH 3 3 42 41.73 7 i-PrOH 4 4 92 4.34 7 i-PrOH 5 5 16 29.25 7 i-PrOH 6 6 66 20.66 7 i-PrOH 2 2 97 847 7 i-PrOH 2 1 88 84.88 7 i-PrOH 2 3 85 81.79 7 i-PrOH 2 4 99 8110 7 i-PrOH 2 5 74 84.611 7 i-PrOH 2 6 99 87.412 7 DCM 1 1 46 68.413 7 DCM 3 3 42 60.714 7 DCM 4 4 26 54.115 7 DCM 5 5 100 79.616 7 DCM 6 6 21 60.517 7 DCM 2 2 100 79.618 7 DCM 2 1 99 86.519 7 DCM 2 3 95 85.620 7 DCM 2 4 96 91.221 7 DCM 2 5 88 85.222 7 DCM 2 6 96 8223 7 EtOAc 1 1 16 1724 7 EtOAc 3 3 26 25.425 7 EtOAc 4 4 4 30.726 7 EtOAc 5 5 13 23.827 7 EtOAc 6 6 22 28.828 7 EtOAc 2 2 79 85.129 7 EtOAc 2 1 64 82.330 7 EtOAc 2 3 57 76.831 7 EtOAc 2 4 62 83.532 7 EtOAc 2 5 43 77.133 7 EtOAc 2 6 61 85.134 7 THF 1 1 23 27.835 7 THF 3 3 22 25.136 7 THF 4 4 7 1937 7 THF 5 5 11 2038 7 THF 6 6 13 49.739 7 THF 2 2 68 83.940 7 THF 2 1 42 68.741 7 THF 2 3 53 67.642 7 THF 2 4 57 78.743 7 THF 2 5 41 62.344 7 THF 2 6 54 83.245 8 i-PrOH 1 1 99 52.746 8 i-PrOH 3 3 99 63.547 8 i-PrOH 4 4 99 24.848 8 i-PrOH 5 5 42 52.9Supplementary data49 8 i-PrOH 6 6 66 57.950 8 i-PrOH 2 2 100 88.651 8 i-PrOH 2 1 98 80.152 8 i-PrOH 2 3 94 78.753 8 i-PrOH 2 4 100 84.554 8 i-PrOH 2 5 74 7555 8 i-PrOH 2 6 99 84.156 8 DCM 1 1 83 68.557 8 DCM 3 3 75 65.758 8 DCM 4 4 43 16.359 8 DCM 5 5 49 77.360 8 DCM 6 6 35 7361 8 DCM 2 2 100 69.962 8 DCM 2 1 100 82.863 8 DCM 2 3 100 83.364 8 DCM 2 4 100 90.865 8 DCM 2 5 100 8266 8 DCM 2 6 100 79.367 8 EtOAc 1 1 62 31.868 8 EtOAc 3 3 49 38.869 8 EtOAc 4 4 20 13.170 8 EtOAc 5 5 32 45.771 8 EtOAc 6 6 25 48.972 8 EtOAc 2 2 91 72.873 8 EtOAc 2 1 74 62.474 8 EtOAc 2 3 67 68.875 8 EtOAc 2 4 75 73.276 8 EtOAc 2 5 53 66.977 8 EtOAc 2 6 67 67.678 8 THF 1 1 44 36.879 8 THF 3 3 52 45.480 8 THF 4 4 12 33.681 8 THF 5 5 20 44.582 8 THF 6 6 29 6783 8 THF 2 2 97 85.384 8 THF 2 1 86 71.885 8 THF 2 3 81 76.486 8 THF 2 4 92 84.987 8 THF 2 5 67 7888 8 THF 2 6 83 81.6Supplementary data β  

Improving conversion and enantioselectivity in hydrogenation by combining different monodentate phosphoramidites; a new combinatorial approach in asymmetric catalysis

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Improving conversion and enantioselectivity in hydrogenation by combining different monodentate phosphoramidites; a new combinatorial approach in asymmetric catalysis

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