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Asymmetric Michael Addition of Unactivated Ketones with β‐Nitrostyrenes Mediated by Bifunctional L‐Prolinamide Organocatalysts
Author(s) -
Rani Dixita,
Bhargava Meha,
Agarwal Jyoti
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202000136
Subject(s) - chemistry , michael reaction , bifunctional , amide , amine gas treating , organocatalysis , catalysis , adduct , addition reaction , ring (chemistry) , substrate (aquarium) , enantioselective synthesis , organic chemistry , combinatorial chemistry , oceanography , geology
The catalytic activity of two types of L‐prolinamide organocatalysts was investigated for asymmetric Michael addition reaction of cyclic/acyclic ketones with β‐nitrostyrens. L‐Prolinamides bearing amino groups on phenyl ring worked well, though their catalytic efficiency as well as selectivity was found to be dependent upon the position of amine group to the amide bond. Organocatalyst having –NH 2 group ortho to amide bond provided the best results. Substrate scope was also studied by performing the reaction of various β‐nitrostyrenes with ketones to afford the corresponding Michael adducts in excellent yields with very high diastereoselectivities and enantioselectivities in almost all cases.