Optically Active Chiral Auxiliary Benzyloxyphenylglycinol for Preparation of Oxazolidine and Its Derivatives

Chemical Research in Chinese Universities ›› 2005, Vol. 21 ›› Issue (4): 476-479.

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Optically Active Chiral Auxiliary Benzyloxyphenylglycinol for Preparation of Oxazolidine and Its Derivatives

FU Ying-huan, CHEN Jin, WU Tong-hao, BAI Xu

The Center for Combinatorial Chemistry and Drug Discovery, Jilin University, Changchun 130012, P. R. China

Received:2004-08-23 Online:2005-07-24 Published:2011-08-06
Supported by:
Supported by Jilin Provincial Fund for Young Talented Scientists(No.20010105) and Changchun Discovery Sciences, Ltd.

Abstract

Abstract: To investigate the recovery of amino alcohols as chiral auxiliaries, optically active p-benzyloxyphenylglycinol and its corresponding oxazolidine of 1-naphthylcarboxaldehyde were prepared. Grignard additions to the oxazolidine followed by electrophilic quench and acidic hydrolysis afforded an aldehyde(compound 8)(later it was reduced to an alcohol, compound 9) in an excellent enantiomeric excess and a good recovery of the chiral amino alcohol. This research provides a model study of chiral amino alcohols in solid phase asymmetric synthesis.

Key words: Chiral auxiliary, p-Benzyloxyphenylglycinol, Grignard addition, Oxazolidine, Asymmetric synthesis

FU Ying-huan, CHEN Jin, WU Tong-hao, BAI Xu. Optically Active Chiral Auxiliary Benzyloxyphenylglycinol for Preparation of Oxazolidine and Its Derivatives[J]. Chemical Research in Chinese Universities, 2005, 21(4): 476-479.

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Optically Active Chiral Auxiliary Benzyloxyphenylglycinol for Preparation of Oxazolidine and Its Derivatives

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