β-Isocupreidine-Catalyzed Asymmetric Baylis−Hillman Reaction of Imines
- 1 August 2003
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (17) , 3103-3105
- https://doi.org/10.1021/ol035102j
Abstract
[reaction: see text] beta-Isocupreidine (beta-ICD)-catalyzed asymmetric Baylis-Hillman reactions of aromatic imines with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) give (S)-enriched N-protected-alpha-methylene-beta-amino acid esters. In contrast to the corresponding aldehydes, imines show the opposite enantioselectivity. A mechanistic proposal governed by hydrogen bonding is presented.Keywords
This publication has 14 references indexed in Scilit:
- Chiral quinuclidine-based amine catalysts for the asymmetric one-pot, three-component aza-Baylis–Hillman reactionTetrahedron Letters, 2003
- Catalytic Asymmetric Syntheses of ICI-199441 and CP-99994 Using Nitro-Mannich ReactionChemistry Letters, 2002
- The First Enantioselective and Diastereoselective Catalytic Nitro-Mannich Reaction: A New Entry to Chiral Vicinal DiaminesSynlett, 2001
- An enantio- and stereocontrolled route to epopromycin B via cinchona alkaloid-catalyzed Baylis–Hillman reactionTetrahedron Letters, 2001
- Novel Asymmetric C−C Bond Formation Process Promoted by Et2AlCl and Its Application to the Stereoselective Synthesis of Unusual β-Branched Baylis−Hillman AdductsThe Journal of Organic Chemistry, 1999
- Substituted sulfonamides via a three component reaction on solid supportTetrahedron Letters, 1998
- Preparation and ring-opening reactions of N-Diphenylphosphinyl aziridinesTetrahedron, 1998
- From Styrenes to Enantiopure α-Arylglycines in Two StepsJournal of the American Chemical Society, 1998
- Cobalt-mediated Reduction of C=N Bond. Synthesis of Methyl N-p-Toluenesulfonyl-1-phenylglycinate Catalyzed by Bis (dioximato)cobalt–Quinine ComplexesChemistry Letters, 1986
- Phosphinamides: a new class of amino protecting groups in peptide synthesisJournal of the Chemical Society, Perkin Transactions 1, 1984