Table of Contents
Organic Chemistry International
Volume 2014, Article ID 982716, 7 pages
http://dx.doi.org/10.1155/2014/982716
Research Article

Stereoselective Synthesis of (+)--Conhydrine from R-(+)-Glyceraldehyde

Fine Chemicals Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500607, India

Received 22 August 2014; Revised 27 September 2014; Accepted 27 September 2014; Published 20 October 2014

Academic Editor: Ashraf Aly Shehata

Copyright © 2014 Nageshwar Rao Penumati and Nagaiah Kommu. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Stereoselective synthesis of (+)-α-Conhydrine was accomplished from protected (R)-(+)-glyceraldehyde, a familiar carbohydrate predecessor. Our synthetic strategy featured the following two key reactions. One is Zn-mediated stereoselective aza-Barbier reaction of imine 6 with allyl bromide to afford chiral homoallylic amine 7, and the other is ring-closing metathesis.