z-logo
Premium
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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here
Accelerating Research

Address

John Eccles House
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom