Enantioselective Aza-Morita-Baylis-Hillman Reaction Using Aliphatic alpha -Amidosulfones as Imine Surrogates
Abermil, Nacim; Masson, Geraldine; Zhu, Jieping
2010

Abstract

The bifunctional catalyst 6'-deoxy-6'-acylamino-beta -isocupreidine served both as a base to trigger the in situ generation of N-sulfonylimine from readily available alpha -amidosulfones and as a chiral nucleophile to initiate the enantioselective aza-Morita-Baylis-Hillman (aza-MBH) reaction. alpha -Methylene-beta -amino-beta -alkyl carbonyl compds., e.g. I, difficultly accessible previously, can now be synthesized in excellent yields and enantioselectivity. [on SciFinder (R)]

Details

Title Enantioselective Aza-Morita-Baylis-Hillman Reaction Using Aliphatic alpha -Amidosulfones as Imine Surrogates
Author(s) Abermil, Nacim ; Masson, Geraldine ; Zhu, Jieping
Published in Advanced Synthesis & Catalysis
Volume 352
Issue 4
Pages 656-660
Date 2010
Publisher Wiley-Blackwell
ISSN 1615-4150
Keywords
Sulfones Role: RCT (Reactant); SPN (Synthetic preparation); PREP (Preparation); RACT (Reactant or reagent) (amido; enantioselective synthesis of alpha -methylene-beta -amino-beta -alkyl carbonyl compds via aza-Morita-Baylis-Hillman reaction using aliph. alpha -amidosulfones as imine surrogates); Addition reaction catalysts (aza-Morita-Baylis-Hillman reaction; stereoselective; enantioselective synthesis of alpha -methylene-beta -amino-beta -alkyl carbonyl compds via aza-Morita-Baylis-Hillman reaction using aliph. alpha -amidosulfones as imine surrogates); Baylis-Hillman reaction (aza-Morita-Baylis-Hillman; stereoselective; enantioselective synthesis of alpha -methylene-beta -amino-beta -alkyl carbonyl compds via aza-Morita-Baylis-Hillman reaction using aliph. alpha -amidosulfones as imine surrogates); Enantioselective synthesis (enantioselective synthesis of alpha -methylene-beta -amino-beta -alkyl carbonyl compds via aza-Morita-Baylis-Hillman reaction using aliph. alpha -amidosulfones as imine surrogates); Esters Role: RCT (Reactant); SPN (Synthetic preparation); PREP (Preparation); RACT (Reactant or reagent) (alpha; beta -unsatd.; enantioselective synthesis of alpha -methylene-beta -amino-beta -alkyl carbonyl compds via aza-Morita-Baylis-Hillman reaction using aliph. alpha -amidosulfones as imine surrogates); enantioselective synthesis methylene aminoalkyl carbonyl compd; amidosulfone vinyl ester enantioselective aza Morita Baylis Hillman reaction
Note CAN 153:358323, 21-2, General Organic Chemistry, Centre de Recherche de Gif, CNRS,Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr., Journal, 1615-4150, written in English., 1191127-87-3P; 1191127-88-4P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (enantioselective synthesis of alpha -methylene-beta -amino-beta -alkyl carbonyl compds via aza-Morita-Baylis-Hillman reaction using aliph. alpha -amidosulfones as imine surrogates); 55-21-0 (Benzamide); 78-94-4 (3-Buten-2-one); 107-02-8 (2-Propenal); 20069-66-3; 34810-13-4 (9-Anthracenecarboxamide); 52684-34-1; 890043-99-9; 1241834-07-0; 1241834-11-6; 1241834-13-8; 1241834-15-0; 1241834-17-2; 1241834-19-4 Role: RCT (Reactant), RACT (Reactant or reagent) (enantioselective synthesis of alpha -methylene-beta -amino-beta -alkyl carbonyl compds via aza-Morita-Baylis-Hillman reaction using aliph. alpha -amidosulfones as imine surrogates); 1056904-24-5P; 1056904-25-6P; 1056904-26-7P; 1056904-27-8P; 1191128-13-8P; 1191128-14-9P; 1191128-15-0P; 1191128-16-1P; 1241833-79-3P; 1241833-84-0P; 1241833-87-3P; 1241833-90-8P; 1241833-93-1P; 1241834-02-5P; 1241834-04-7P Role: SPN (Synthetic preparation), PREP (Preparation) (enantioselective synthesis of alpha -methylene-beta -amino-beta -alkyl carbonyl compds via aza-Morita-Baylis-Hillman reaction using aliph. alpha -amidosulfones as imine surrogates)
DOI https://doi.org/10.1002/adsc.200900900
Laboratories LSPN
Record Appears in Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date 2010-11-25