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A General, Enantioselective Synthesis of 1-Azabicyclo[m.n.0]alkane Ring Systems.
MedLine Citation:
PMID:  23459400     Owner:  NLM     Status:  Publisher    
In this Letter, we describe a novel approach for the general and enantioselective synthesis of a diverse array of small to large 1-azabicyclo[m.n.0]alkyl ring systems with an embedded olefin handle for further functionalization. The stereochemistry is established via a highly diastereoselective indium-mediated allylation of an Ellman sulfinimine in greater than 9:1 dr., which is readily separable by column chromatography to afford a single diastereomer. This methodology allows for the rapid preparation of 1-azabicyclo[m.n.0]alkane ring systems that are not readily accessible through any other chemistry in excellent overall yields and, for many systems, the only enantioselective preparation reported to date.
Timothy J Senter; Michael L Schulte; Leah C Konkol; Tyler E Wadzinski; Craig W Lindsley
Publication Detail:
Journal Detail:
Title:  Tetrahedron letters     Volume:  54     ISSN:  0040-4039     ISO Abbreviation:  Tetrahedron Lett.     Publication Date:  2013 Mar 
Date Detail:
Created Date:  2013-3-5     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2984819R     Medline TA:  Tetrahedron Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  1645-1648     Citation Subset:  -    
Department of Chemistry, Vanderbilt University, Nashville, TN 37232, USA.
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