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Stereospecific Construction of Contiguous Quaternary All‐Carbon Centers by Oxidative Ring Contraction
Author(s) -
Yu Xin,
Hu Jiadong,
Shen Zhigao,
Zhang Hui,
Gao JinMing,
Xie Weiqing
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201609975
Subject(s) - regioselectivity , stereospecificity , oxidative phosphorylation , chemistry , quaternary carbon , contraction (grammar) , stereochemistry , ring (chemistry) , organic chemistry , enantioselective synthesis , biology , biochemistry , catalysis , endocrinology
Oxidative ring contraction of cyclic α‐formyl ketones was facilitated by the action of H 2 O 2 under operationally simple and environmentally benign reaction conditions. The process was highly regioselective and enables stereospecific construction of contiguous quaternary all‐carbon centers from stereodefined all‐substituted all‐cyclic ketones. The asymmetric syntheses of (+)‐cuparene and (+)‐tochuinyl acetate were also successively achieved by taking advantage of this novel protocol.