Sterically Biased 3,3-Sigmatropic Rearrangement of Azides:  Efficient Preparation of Nonracemic α-Amino Acids and Heterocycles

Homochiral α-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...

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Bibliographic Details
Published in:Organic letters 2005-10, Vol.7 (21), p.4769-4771
Main Authors: Gagnon, David, Lauzon, Sophie, Godbout, Cédrickx, Spino, Claude
Format: Article
Language:English
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Summary:Homochiral α-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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol052034n