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Organocatalytic synthesis of 5‐hydroxyisoxazolidine catalyzed by camphor sulfonyl hydrazines through aza‐Michael addition/cyclization
Author(s) -
Xu FangFang,
Chen LingYan,
Sun Peng,
Lv Yixin,
Zhang YanXue,
Li JiaYu,
Yin Xiaoying,
Li Ya
Publication year - 2020
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.23168
Subject(s) - chemistry , sulfonyl , camphor , michael reaction , catalysis , hydrazine (antidepressant) , enantiomer , enantioselective synthesis , organic chemistry , enantiomeric excess , chromatography , alkyl
A series of chiral 5‐hydroxy isoxazolidines has been successfully synthesized through camphor sulfonyl hydrazine‐catalyzed asymmetric aza‐Michael addition reaction between N , O ‐protected hydroxyamines and enals. Moderate yields with moderate to good enantioselectivities (up to 96% enantiomeric excess [ee]) were achieved. It provides an alternative asymmetric approach to preparing isoxazolidine derivatives.