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Asymmetric Synthesis of Spiropyrazolones through Phosphine‐Catalyzed [4+1] Annulation
Author(s) -
Han Xiaoyu,
Yao Weijun,
Wang Tianli,
Tan Yong Ren,
Yan Ziyu,
Kwiatkowski Jacek,
Lu Yixin
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201311214
Subject(s) - annulation , synthon , phosphine , enantioselective synthesis , pyrazolones , chemistry , catalysis , organocatalysis , combinatorial chemistry , organic chemistry , medicinal chemistry , stereochemistry
An enantioselective synthesis of spiropyrazolones from allenoate‐derived MBH acetates and pyrazolones through a phosphine‐mediated [4+1] annulation process has been developed. Spiropyrazolones were readily prepared in good chemical yields and good to high enantioselectivities. This is the first asymmetric example in which α‐substituted allenoates were utilized as a C 4 synthon for phosphine‐catalyzed [4+1] annulation.