Document Detail

Sterically biased 3,3-sigmatropic rearrangement of azides: efficient preparation of nonracemic alpha-amino acids and heterocycles.
MedLine Citation:
PMID:  16209531     Owner:  NLM     Status:  PubMed-not-MEDLINE    
[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.
David Gagnon; Sophie Lauzon; Cédrickx Godbout; Claude Spino
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Organic letters     Volume:  7     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2005 Oct 
Date Detail:
Created Date:  2005-10-07     Completed Date:  2006-08-08     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4769-71     Citation Subset:  -    
Département de Chimie, Université de Sherbrooke, Sherbrooke, QC, Canada J1K 2R1.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

Previous Document:  A Ru-catalyzed tandem alkyne-enone coupling/Michael addition: synthesis of 4-methylene-2,6-cis-tetra...
Next Document:  Highly diastereoselective templated complexation of dipyrromethenes.