Invertible Enantioselectivity in 6'-Deoxy-6'-acylamino-beta -isocupreidine-Catalyzed Asymmetric Aza-Morita-Baylis-Hillman Reaction: Key Role of Achiral Additive
Abermil, Nacim; Masson, Geraldine; Zhu, Jieping
2009

Abstract

The beta -isocupreidine (beta -ICD) or beta -ICD-amide (I)-catalyzed aza-Morita-Baylis-Hillman reaction between N-sulfonylimines and alkyl vinyl ketones produced the (R)-enriched adducts, e.g. II. By adding a catalytic amt. of beta -naphthol, the enantioselectivity of the same reaction was inversed leading to (S)-isomers in excellent yields and enantioselectivities. Both arom. and aliph. imines are accepted as substrates for this reaction. [on SciFinder (R)]

Details

Title Invertible Enantioselectivity in 6'-Deoxy-6'-acylamino-beta -isocupreidine-Catalyzed Asymmetric Aza-Morita-Baylis-Hillman Reaction: Key Role of Achiral Additive
Author(s) Abermil, Nacim ; Masson, Geraldine ; Zhu, Jieping
Published in Organic Letters
Volume 11
Issue 20
Pages 4648-4651
Date 2009
ISSN 1523-7060
Keywords
Baylis-Hillman reaction; Baylis-Hillman reaction catalysts; Reaction mechanism; Stereoselective synthesis (invertible enantioselectivity achieved by achiral additive beta -naphthol in the asym. synthesis of sulfonyl allylamides via acylamino-beta -isocupreidine-catalyzed asym. aza-Morita-Baylis-Hillman reaction of sulfonylimines and alkyl vinyl ketones); Sulfonamides Role: SPN (Synthetic preparation); PREP (Preparation) (invertible enantioselectivity achieved by achiral additive beta -naphthol in the asym. synthesis of sulfonyl allylamides via acylamino-beta -isocupreidine-catalyzed asym. aza-Morita-Baylis-Hillman reaction of sulfonylimines and alkyl vinyl ketones); Imides; Sulfonic acids Role: RCT (Reactant); RACT (Reactant or reagent) (sulfonimides; invertible enantioselectivity achieved by achiral additive beta -naphthol in the asym. synthesis of sulfonyl allylamides via acylamino-beta -isocupreidine-catalyzed asym. aza-Morita-Baylis-Hillman reaction of sulfonylimines and alkyl vinyl ketones); Ketones Role: RCT (Reactant); SPN (Synthetic preparation); PREP (Preparation); RACT (Reactant or reagent) (alpha; beta -unsatd.; invertible enantioselectivity achieved by achiral additive beta -naphthol in the asym. synthesis of sulfonyl allylamides via acylamino-beta -isocupreidine-catalyzed asym. aza-Morita-Baylis-Hillman reaction of sulfonylimines and alkyl vinyl ketones); sulfonyl allylamide asym prepn; sulfonylimine vinyl ketone asym aza Morita Baylis Hillman addn; acylamino isocupreidine catalyst naphthol achiral additive invertible enantioselectivity mechanism
Note CAN 151:469813
25-13
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
1191127-86-2P; 1191127-87-3P; 1191127-88-4P; 1191127-89-5P Role: CAT (Catalyst use), SPN (Synthetic preparation), PREP (Preparation), USES (Uses) (invertible enantioselectivity achieved by achiral additive beta -naphthol in the asym. synthesis of sulfonyl allylamides via acylamino-beta -isocupreidine-catalyzed asym. aza-Morita-Baylis-Hillman reaction of sulfonylimines and alkyl vinyl ketones); 135-19-3 (beta -Naphthol) Role: MOA (Modifier or additive use), USES (Uses) (invertible enantioselectivity achieved by achiral additive beta -naphthol in the asym. synthesis of sulfonyl allylamides via acylamino-beta -isocupreidine-catalyzed asym. aza-Morita-Baylis-Hillman reaction of sulfonylimines and alkyl vinyl ketones); 55-21-0 (Benzamide); 78-94-4 (Methyl vinyl ketone); 541-46-8; 1629-58-9 (Ethyl vinyl ketone); 2243-82-5 (2-Naphthalenecarboxamide); 34810-13-4 (9-Anthracenecarboxamide); 73845-03-1; 861145-19-9; 861145-33-7; 890043-99-9; 1023288-03-0; 1191127-92-0; 1191127-93-1; 1191127-94-2; 1191127-95-3; 1191127-96-4; 1191127-97-5; 1191127-98-6; 1191127-99-7; 1191128-00-3; 1191128-01-4 Role: RCT (Reactant), RACT (Reactant or reagent) (invertible enantioselectivity achieved by achiral additive beta -naphthol in the asym. synthesis of sulfonyl allylamides via acylamino-beta -isocupreidine-catalyzed asym. aza-Morita-Baylis-Hillman reaction of sulfonylimines and alkyl vinyl ketones); 1191127-90-8P; 1191127-91-9P; 1191128-02-5P; 1191128-03-6P; 1191128-04-7P; 1191128-05-8P; 1191128-06-9P; 1191128-07-0P; 1191128-08-1P; 1191128-09-2P; 1191128-10-5P; 1191128-11-6P; 1191128-12-7P; 1191128-13-8P; 1191128-14-9P; 1191128-15-0P; 1191128-16-1P; 1191128-17-2P; 1191128-18-3P; 1191128-19-4P; 1191128-20-7P Role: SPN (Synthetic preparation), PREP (Preparation) (invertible enantioselectivity achieved by achiral additive beta -naphthol in the asym. synthesis of sulfonyl allylamides via acylamino-beta -isocupreidine-catalyzed asym. aza-Morita-Baylis-Hillman reaction of sulfonylimines and alkyl vinyl ketones)
DOI https://doi.org/10.1021/ol901920s
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