Liquid-Phase Synthesis of Chiral Tartrate Ligand Library for Enantioselective Sharpless Epoxidation of Allylic Alcohols

This paper reports a successful development of a group of efficient soluble polymer-supported chiral tartrate ligands by liquid-phase synthesis for Sharpless epoxidation of a variety of allylic alcohols through ligand diversity. The influence of substituent in chiral tartrate ligands on the enantios...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-03, Vol.69 (6), p.2042-2047
Main Authors: Guo, Hong-Chao, Shi, Xue-Yan, Wang, Xian, Liu, Shang-Zhong, Wang, Min
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:This paper reports a successful development of a group of efficient soluble polymer-supported chiral tartrate ligands by liquid-phase synthesis for Sharpless epoxidation of a variety of allylic alcohols through ligand diversity. The influence of substituent in chiral tartrate ligands on the enantioselectivities of the reaction was disclosed. Moderate chemical yields and good enantiomeric excesses were obtained by using soluble polymer-supported tartrate ester in the epoxidation of allylic alcohols with Ti(O-i-Pr)4/tert-butyl hydroperoxide.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo035818s