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Highly Enantioselective Synthesis of ( R )‐3‐Alkyl‐3‐hydroxyindolin‐2‐ones Including Natural Product ( R )‐Convolutamydine A Catalyzed by A Primary Amine
Author(s) -
Guo JunTao,
Zhang BaoQiang,
Luo Yuan,
Guan Zhi,
He YanHong
Publication year - 2017
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.201700019
Subject(s) - chemistry , yield (engineering) , amine gas treating , enantioselective synthesis , catalysis , alkyl , primary (astronomy) , natural product , organic chemistry , combinatorial chemistry , materials science , physics , astronomy , metallurgy
An efficient strategy for constructing ( R )‐3‐alkyl‐3‐hydroxyindolin‐2‐one derivatives catalyzed by a structurally simple and easily prepared primary amine catalyst under mild conditions has been developed. Various isatins and ketones were tolerated, and the desired products were obtained in up to 99 % yield and up to 99 % ee . The biologically active natural product ( R )‐convolutamydine A was synthesized in 96 % yield and 95 % ee .