Premium
Theoretical study on the reaction mechanisms of Michael chirality addition between propionaldehyde and nitroalkene catalyzed by an enantioselective catalyst
Author(s) -
Zhou Xinming,
Li Ling,
Sun Xuejun,
Wang Yajun,
Du Dongmei,
Fu Hui
Publication year - 2018
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22844
Subject(s) - chemistry , nitroalkene , enantioselective synthesis , propionaldehyde , michael reaction , catalysis , chirality (physics) , stereochemistry , computational chemistry , organic chemistry , aldehyde , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
Abstract The asymmetric Michael addition between propionaldehyde and nitroalkene catalyzed by 8‐(ethoxycarbonyl)‐1,2,3,3a,8,8a‐hexahydropyrrolo[2,3‐b]indole‐2‐carboxylic acid has obtained relatively high yields and excellent enantioselectivities at room temperature. In this study, the molecular structures and optical activity of the most stable conformation I are optimized at B3LYP/6‐311++ G(d,p) level. We find that levorotatory conformation I catalyzing the same Michael addition can produce laevo‐product A and dextrorotatory conformation I′ can obtain the dextral‐product A'. These results have guiding significance for further studying on the new chemzymes and the mechanism of the obtained different chiral products.