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Oxidant‐Resistant Hydrogen‐Bond‐Donating Organocatalyst for Enantioselective Nucleophilic Epoxidation of α,β‐Unsaturated Amides
Author(s) -
Kobayashi Yusuke,
Li Shanji,
Takemoto Yoshiji
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201400031
Subject(s) - chemistry , enantioselective synthesis , bifunctional , nucleophile , organocatalysis , catalysis , organic chemistry , hydrogen bond , nucleophilic addition , combinatorial chemistry , molecule
Bifunctional benzothiadiazine‐catalyzed epoxidation of α,β‐unsaturated amides proceeds efficiently to give chiral 2‐oxiranecarboxamides in excellent yields of 89–99 % and with good enantioselectivity of up to 84 % ee . A synthetic application of the oxiranecarboxamides is also described.