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Enantioselective Synthesis of Optically Active O ‐Benzoyl‐Protected α‐Hydroxyl‐β,γ‐Unsaturated Acids with Chiral Induction of ( S )‐Glyceraldehyde Acetonide
Author(s) -
Liu Ruiquan,
Wang Lei,
Li Qibo,
Liao Min,
Yang Zhikun,
Huang Yun,
Zheng Bing,
Bian Qinghua,
Wang Min,
Liu Shangzhong
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702244
Subject(s) - optically active , chemistry , enantioselective synthesis , acetonide , yield (engineering) , organic chemistry , catalysis , biology , triamcinolone acetonide , materials science , metallurgy , immunology
α‐Hydroxyl‐β,γ‐unsaturated acids are usually present in biologically active natural products and medicines, and serve as valuable building blocks in synthetic organic chemistry. A new method for the synthesis of O ‐benzoyl‐protected α‐hydroxyl‐β,γ‐unsaturated acids is presented. Chiral induction was achieved using ( S )‐glyceraldehyde acetonide as chiral source together with ClTi(O i ‐Pr) 3 as coordinating agent. The overall synthetic route included 6 simple steps, and six optically active O ‐benzoyl‐protected α‐hydroxyl‐β,γ‐unsaturated acids 1 a ‐ 1 f (99% ee ) were prepared in up to 53% yield.