Table of Contents
Organic Chemistry International
Volume 2010, Article ID 452956, 3 pages
Research Article

Directed Metalation of Heterocycles, 5-Methoxy-2-phenyloxazol-4-yllithium: An Approach to , -Dehydroamino Acids

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India

Received 1 July 2009; Accepted 16 September 2009

Academic Editor: Kirpal Bisht

Copyright © 2010 Sosale Chandrasekhar and Malempati Srimannarayana. 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.


5-Methoxy-2-phenyloxazole was deprotonated at (by -BuLi or LDA, in THF at −78 ). The resulting anion was generally unreactive to alkylation (except methylation with MeI-TMEDA) but added to PhCHO and CHCHO. The alcohols thus produced dehydrated and ring opened in acid, to the corresponding , -dehydroamino acids in moderate overall yields.