Document Detail


Stereoselective synthesis of chiral 4-(1-chloroalkyl)-beta-lactams starting from amino acids and their transformation into functionalized chiral azetidines and pyrrolidines.
MedLine Citation:
PMID:  20704284     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Chiral short-chain alpha-chloroaldehydes were prepared starting from enantiomerically pure amino acids in a three-step approach, thus providing a practical synthetic alternative for known organocatalytic alpha-chlorination procedures. The latter aldehydes proved to be useful starting materials for the stereoselective Staudinger synthesis of (3S,4S)-4-[(1S)-1-chloroalkyl]azetidin-2-ones in high diastereomeric ratios and good overall yields, which were used as chiral building blocks for the preparation of a number of azetidines and pyrrolidines.
Authors:
Stijn Dekeukeleire; Matthias D'hooghe; Karl W Törnroos; Norbert De Kimpe
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Sep 
Date Detail:
Created Date:  2010-08-27     Completed Date:  2010-12-08     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  5934-40     Citation Subset:  IM    
Affiliation:
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium.
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MeSH Terms
Descriptor/Qualifier:
Amino Acids / chemistry*
Azetidines / chemistry*
Molecular Conformation
Pyrrolidines / chemistry*
Stereoisomerism
beta-Lactams / chemical synthesis*,  chemistry
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Azetidines; 0/Pyrrolidines; 0/beta-Lactams

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