Palladium-Catalyzed, Copper(I)-Mediated Coupling of Boronic Acids and Benzylthiocyanate. A Cyanide-Free Cyanation of Boronic Acids

A new method for the synthesis of nitriles is described. As a complement to the classic cyanation of aryl halides using cyanide sources and a transition metal catalyst, the palladium-catalyzed cross-coupling of thiocyanates with boronic acids in the presence of copper(I) thiophene-2-carboxylate (CuTC) affords nitriles in good to excellent yields

A Synthesis of Trisquinones

A Synthesis of Trisquinone

A New Reaction Motif: “Homo-S_N2′-Like” Direct Nucleophilic Addition to Neutral η³-Allylmolybdenum Complexes. Total Synthesis of the Antimalarial (+)-Isofebrifugine

A New Reaction Motif: “Homo-SN2′-Like” Direct Nucleophilic Addition to Neutral η3-Allylmolybdenum Complexes. Total Synthesis of the Antimalarial (+)-Isofebrifugin

A Concise and Scalable Synthesis of High Enantiopurity (−)-d-<i>erythro</i>-Sphingosine Using Peptidyl Thiol Ester−Boronic Acid Cross-Coupling

A short and efficient synthesis of high enantiopurity (−)-d-erythro-sphingosine has been achieved in 71% yield over 6 steps from N-Boc-l-serine. The key steps are high yield, racemization-free, palladium-catalyzed, copper(I)-mediated coupling of the thiophenyl ester of N-Boc-O-TBS l-serine with E-1-pentadecenyl boronic acid and the highly diastereoselective reduction of the resulting peptidyl ketone with LiAl(O-t-Bu)3H. By using this concise route (−)-d-erythro-sphingosine can be prepared on large scale and in high enantio- and diastereopurity (ee >99%, de up to 99%)

Heteroaromatic Thioether−Organostannane Cross-Coupling

Heteroaromatic thioethers and aryl, heteroaryl, and alkenylstannanes participate in a palladium-catalyzed, copper(I)-mediated cross-coupling reaction at 50 °C in THF

Synthesis of Substituted Oxa- and Aza[3.2.1] and [4.3.1]Bicyclics via an Unprecedented Molybdenum-Mediated 1,5-“Michael-Type” Reaction

The direct internal nucleophilic functionalization of a π-bound carbon of neutral TpMo(CO)2(5-oxo-η3-pyranyl) and TpMo(CO)2(5-oxo-η3-pyridinyl) complexes by enolates represents a new reaction profile for neutral TpMo(CO)2(η3-allyl) complexes. This Mo-mediated “1,5-Michael reaction” proceeds in good to excellent yields and provides, after demetalation, a new and efficient synthetic approach to oxa- and aza[3.2.1]bicyclics of high enantiomeric purity

Enantiocontrolled [5 + 2] Cycloaddition to η³-Pyranylmolybdenum π-Complexes. Synthesis of Substituted Oxabicyclo[3.2.1]octenes of High Enantiopurity

Enantiocontrolled [5 + 2] Cycloaddition to η3-Pyranylmolybdenum π-Complexes. Synthesis of Substituted Oxabicyclo[3.2.1]octenes of High Enantiopurit

Organometallic Enantiomeric Scaffolding: Organometallic Chirons. Total Synthesis of (−)-Bao Gong Teng A by a Molybdenum-Mediated [5+2] Cycloaddition

Bao Gong Teng A, an optically active tropane alkaloid with hypotensive and miotic activity isolated from the Chinese herb Erycibe obtusifolia Benth, was synthesized by an “organometallic chiron” strategy in which single enantiomers of TpMo(CO)2(η3-pyridinyl) complexes are produced in quantity and then elaborated easily and efficiently to generate, after demetalation, highly enantiopure advanced synthetic intermediates possessing the tropane core

Synthesis of Substituted Oxa- and Aza[3.2.1] and [4.3.1]Bicyclics via an Unprecedented Molybdenum-Mediated 1,5-“Michael-Type” Reaction

The direct internal nucleophilic functionalization of a π-bound carbon of neutral TpMo(CO)2(5-oxo-η3-pyranyl) and TpMo(CO)2(5-oxo-η3-pyridinyl) complexes by enolates represents a new reaction profile for neutral TpMo(CO)2(η3-allyl) complexes. This Mo-mediated “1,5-Michael reaction” proceeds in good to excellent yields and provides, after demetalation, a new and efficient synthetic approach to oxa- and aza[3.2.1]bicyclics of high enantiomeric purity

A Synthesis of Trisquinones

A Synthesis of Trisquinone