Document Detail

N-Carbamate-assisted stereoselective synthesis of chiral vicinal amino sulfides.
MedLine Citation:
PMID:  11922827     Owner:  NLM     Status:  MEDLINE    
[reaction: see text] Simply mixing amino alcohol A and thiol in toluene and TFA provided the corresponding amino sulfide B in excellent chemical yield and diastereoselectivity. A double SN2 process initiated by O-5 participation of the neighboring N-carbamate group was advanced to explain the overall retention of configuration at the chiral benzylic center.
Michaël De Paolis; Jörg Blankenstein; Michèle Bois-Choussy; Jieping Zhu
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Organic letters     Volume:  4     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2002 Apr 
Date Detail:
Created Date:  2002-03-29     Completed Date:  2002-05-23     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1235-8     Citation Subset:  IM    
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
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MeSH Terms
Amines / chemical synthesis*
Benzyl Compounds / chemical synthesis*
Carbamates / chemistry*
Indicators and Reagents
Magnetic Resonance Spectroscopy
Sulfides / chemical synthesis*
Reg. No./Substance:
0/Amines; 0/Benzyl Compounds; 0/Carbamates; 0/Indicators and Reagents; 0/Sulfides

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

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