Document Detail


Synthesis of Anti-beta-substituted gamma,delta-unsaturated amino acids via Eschenmoser-Claisen rearrangement.
MedLine Citation:
PMID:  16956190     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Anti-beta-substituted gamma,delta-unsaturated amino acids have been synthesized via a novel design of the Eschenmoser-Claisen rearrangement. The rearrangement gives good isolated yields and excellent diastereoselectivity due to (Z)-N,O-ketene acetal formation and the pseudochairlike conformations of the reaction intermediates. Upon reductive hydrolysis, important novel amino acids and amino alcohols were synthesized for the first time via this methodology.
Authors:
Hongchang Qu; Xuyuan Gu; Byoung J Min; Zhihua Liu; Victor J Hruby
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural    
Journal Detail:
Title:  Organic letters     Volume:  8     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2006 Sep 
Date Detail:
Created Date:  2006-09-07     Completed Date:  2007-07-09     Revised Date:  2014-09-14    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4215-8     Citation Subset:  IM    
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Amino Acids / chemical synthesis*
Magnetic Resonance Spectroscopy
Stereoisomerism
Grant Support
ID/Acronym/Agency:
DA 06284/DA/NIDA NIH HHS; DA 13449/DA/NIDA NIH HHS; DK 17420/DK/NIDDK NIH HHS; P01 DA006284/DA/NIDA NIH HHS; P01 DA006284-17/DA/NIDA NIH HHS; R01 DA013449/DA/NIDA NIH HHS; R01 DA013449-08/DA/NIDA NIH HHS; R01 DK017420/DK/NIDDK NIH HHS; R01 DK017420-32/DK/NIDDK NIH HHS
Chemical
Reg. No./Substance:
0/Amino Acids
Comments/Corrections

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


Previous Document:  A dibenzofuran-based host material for blue electrophosphorescence.
Next Document:  Achieving high selectivity and facile displacement with a new thiol auxiliary for boron-mediated ald...