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Synthesis of Chiral α ‐Benzyl‐ β 2 ‐hydroxy Carboxylic Acids through Iridium‐Catalyzed Asymmetric Hydrogenation of α ‐Oxymethylcinnamic Acids
Author(s) -
Li ZeYu,
Song Song,
Zhu ShouFei,
Guo Na,
Wang LiXin,
Zhou QiLin
Publication year - 2014
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201400361
Subject(s) - chemistry , iridium , asymmetric hydrogenation , oxazoline , catalysis , phosphine , reactivity (psychology) , enantioselective synthesis , organic chemistry , natural product , combinatorial chemistry , medicinal chemistry , medicine , alternative medicine , pathology
Abstract An asymmetric hydrogenation of α ‐oxymethylcinnamic acids was developed by using chiral spiro phosphine‐oxazoline/iridium complexes as catalysts to prepare β 2 ‐hydroxycarboxylic acids with high reactivity (TON up to 2000) and excellent enantioselectivity (up to 99.5% ee ). By using this highly efficient asymmetric hydrogenation as a key step, a concise total synthesis of natural product homoisoflavone ( S )‐(+)‐ 4 was accomplished.