Document Detail

Synthesis of enantiopure trans-N-Boc-3-aminobicyclo[2.2.2]octane-2-carboxylic acids and their bicyclic 1,3-amino alcohol derivatives via the [4+2] cycloaddition of 1,3-cyclohexadiene to a chiral β-nitroacrylate.
MedLine Citation:
PMID:  20928894     Owner:  NLM     Status:  In-Data-Review    
The chiral β-nitroacrylate 2 derived from the (R)- or (S)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl) benzoic acid 1 acts as a reactive dienophile in a diastereoselective Diels-Alder reaction with 1,3-cyclohexadiene. The major cycloadducts have been isolated and transformed into enantiopure trans(2S,3S)- or (2R,3R)-N-Boc-3-aminobicyclic[2,2,2]octane-2-carboxylic acids 5. The trans-(2S,3S)- or (2R,3R)-N-Boc 3-(hydoxymethyl)-2-aminobicyclic[2,2,2]octane 6 derivatives were also obtained. Chirality, 2011. © 2010 Wiley-Liss, Inc.
Monique Calmes; Françoise Escale; Claude Didierjean; Jean Martinez
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Publication Detail:
Type:  Journal Article     Date:  2010-10-06
Journal Detail:
Title:  Chirality     Volume:  23     ISSN:  1520-636X     ISO Abbreviation:  Chirality     Publication Date:  2011 Mar 
Date Detail:
Created Date:  2011-02-09     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8914261     Medline TA:  Chirality     Country:  United States    
Other Details:
Languages:  eng     Pagination:  245-9     Citation Subset:  IM    
Copyright Information:
Copyright © 2010 Wiley-Liss, Inc.
Institut des Biomolécules Max Mousseron (IBMM) UMR 5247 CNRS-UM1-UM2, Université Montpellier 2, Bâtiment Chimie (17), 34095 Montpellier cedex 5, France.
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