Document Detail


Selective synthesis of either enantiomer of alpha-amino acids by switching the regiochemistry of the tricyclic iminolactones prepared from a single chiral source.
MedLine Citation:
PMID:  12530907     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
Preparation of l-alpha-amino acids was easily accomplished simply by exchanging the position of the lactone group of our recently reported chiral template 1 from C2 to C3. The new chiral template 7 was prepared in 54% overall yield over five steps from (1R)-(+)-camphor. Alkylation of iminolactone 7 afforded the alpha-monosubstituted products in good yields and excellent diastereoselectivities (>98%). Hydrolysis of the alkylated iminolactones furnished the desired l-alpha-amino acids in good yields and ee with nearly quantitative recovery of chiral auxiliary 4.
Authors:
Peng-Fei Xu; Ta-Jung Lu
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  68     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2003 Jan 
Date Detail:
Created Date:  2003-01-17     Completed Date:  2003-07-07     Revised Date:  2003-11-04    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  658-61     Citation Subset:  -    
Affiliation:
Department of Chemistry, National Chung-Hsing University, Taichung, Taiwan 40227, Republic of China.
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