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Organocatalytic Enantioselective Stereoablative Hydroxylation of 3‐Halooxindoles: An Effective Method for the Construction of Enantioenriched 3‐Substituted 3‐Hydroxy‐2‐Oxindoles
Author(s) -
Liao YuHua,
Wu ZhiJun,
Han WenYong,
Zhang XiaoMei,
Yuan WeiCheng
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201201395
Subject(s) - enantioselective synthesis , hydroxylation , nucleophile , electrophile , chemistry , organocatalysis , combinatorial chemistry , catalysis , optically active , organic chemistry , enzyme
3‐Substituted oxindoles as electrophilic partners : An unprecedented method for the construction of hydroxylated 3‐substituted oxindoles in high yields and excellent enantioselectivities through stereoablative hydroxylation of 3‐halooxindoles with an organocatalyst has been developed. This process not only differs from the common convention of using 3‐substituted oxindoles as nucleophiles, but also provides a viable entry to optically active 3‐substituted 3‐hydroxy‐2‐oxindoles (see scheme).