New bifunctional substrates for Copper-catalysed asymmetric conjugate addition reactions with trialkylaluminium

Article Article scientifique Article New bifunctional substrates for Copper-catalysed asymmetric conjugate addition reactions with trialkylaluminium eng 2009 author Ladjel Chehla 561772 author Fuchs Nicolas 504328 author Zhao Jinkai 532810 author Bernardinelli Gérald Hugues 24765 author Alexakis Alexandre 123950 4949-4955 10.1002/ejoc.200900662 1099-0690 Trialkylaluminium reagents have been found to undergo a copper-catalyzed asymmetric conjugate addition (ACA) reaction with oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylates with the simultaneous creation of two stereocenters. Different types of ligands were tested, and chiral phosphoramidite ligands allowed the reaction to proceed with good yields and good to excellent enantioselectivity. The syn substitution product observed by X-ray analysis suggests an exo attack of the nucleophile. Herein we report the results obtained in the development of this copper-catalyzed ACA methodology, which affords an all-carbon quaternary center with unsubstituted and substituted oxacyclic Michael acceptors. The study was completed by mechanistic investigations performed to elucidate the original reaction pathway. Conjugation Copper P ligands Aluminium Oxygen heterocycles Dewey 540 36 Département de chimie organique 141 false European journal of organic chemistry 29 799022eb-25d0-4a7b-bd09-548f630edb85 Article (Published version) Restricted file1.pdf 9923 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Title	Published in	Access level	OA Policy	Year	Views	Downloads

New bifunctional substrates for Copper-catalysed asymmetric conjugate addition reactions with trialkylaluminium	European journal of organic chemistry			2009	490	0

Archive ouverte UNIGE

Zhao, Jinkai