Absolute configuration of conhydrine

Author:

Fodor G.,Bauerschmidt E.,Craig J. Cymerman

Abstract

Catalytic hydrogenation of optically active 2-pyridyl ethylcarbinol (1) formed the alkaloid conhydrine (2) stereospecifically. Application of the von Braun reaction gave conversion of (+)-conhydrine into R-(−)-3-octyl benzoate and of (−)-conhydrine into the S-(+)-antimer. Both the relative and absolute configuration of the two asymmetric centers in natural (+)-conhydrine have been determined by the combined use of optical rotatory dispersion (o.r.d.) and circular dichroism (c.d.). The results are in agreement with other physical and chemical evidence.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Cited by 19 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Substrate induced diastereoselective hydrogenation/reduction of arenes and heteroarenes;RSC Advances;2016

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