Document Detail

Stereoselective synthesis of unnatural spiroisoxazolinoproline-based amino acids and derivatives.
MedLine Citation:
PMID:  12153267     Owner:  NLM     Status:  MEDLINE    
A route to spiroisoxazolinoproline-based amino acid derivatives is reported in which exo-methyleneprolinate 4 (tert-butyl ester) reacts as a dipolarophile with nitrile oxides to generate spiroisoxazolinoprolinates 7/10/11 in good yields (70-75%) and with ca. 1:4 cis:trans diastereoselectivity. tert-Butyl spiroisoxazolinoprolinates were separable by column chromatography and amenable to scale-up leading to single diastereoisomers of N-Boc and N-Fmoc protected spiroisoxazolinoproline amino acids.
Wei-Chieh Cheng; Yannan Liu; Melissa Wong; Marilyn M Olmstead; Kit S Lam; Mark J Kurth
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  67     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2002 Aug 
Date Detail:
Created Date:  2002-08-02     Completed Date:  2002-09-20     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  5673-7     Citation Subset:  IM    
Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616-5295, USA.
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MeSH Terms
Amino Acids / chemical synthesis*,  chemistry
Models, Molecular
Molecular Conformation
Proline / analogs & derivatives*,  chemistry
Structure-Activity Relationship
Reg. No./Substance:
0/Amino Acids; 0/Oxazoles; 147-85-3/Proline

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