Sterically Biased 3,3-Sigmatropic Rearrangement of Azides: Efficient Preparation of Nonracemic α-Amino Acids and Heterocycles
Organic Letters2005Vol. 7(21), pp. 4769–4771
Citations Over TimeTop 22% of 2005 papers
Abstract
[reaction: see text] Homochiral alpha-amino acids, heterocycles, and carbocycles are efficiently constructed via a short sequence of reactions starting from the chiral auxiliary p-menthane-3-carboxaldehyde. The key feature of the sequence is a highly selective tandem Mitsunobu/3,3-sigmatropic rearrangement of hydrazoic acid that procures enantiomerically enriched allylic azides. The sequence is either terminated by oxidative cleavage to provide amino acids or by ring-closing metathesis to provide heterocycles or carbocycles bearing nitrogen.
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