Synthesis of Chiral  α ‐Benzyl‐ β  2 ‐hydroxy Carboxylic Acids through Iridium‐Catalyzed Asymmetric Hydrogenation of  α ‐Oxymethylcinnamic Acids | Zendy

Li ZeYu | Zendy; Song Song | Zendy; Zhu ShouFei | Zendy; Guo Na | Zendy; Wang LiXin | Zendy; Zhou QiLin | Zendy

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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

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.

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