research article

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
Organic Letters

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)]

Type
research article
DOI
10.1021/ol901920s
Author(s)
Abermil, Nacim
•
Masson, Geraldine
•
Zhu, Jieping  
Date Issued

2009

Published in
Organic Letters
Volume

11

Issue

20

Start page

4648

End page

4651

Subjects

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)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LSPN  
Available on Infoscience
November 25, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/58408