Document Detail


The origin of enantioselectivity in the l-threonine-derived phosphine-sulfonamide catalyzed aza-Morita-Baylis-Hillman reaction: effects of the intramolecular hydrogen bonding.
MedLine Citation:
PMID:  23774825     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
l-Threonine-derived phosphine-sulfonamide was identified as the most efficient catalyst to promote enantioselective aza-Morita-Baylis-Hillman (MBH) reactions, affording the desired aza-MBH adducts with excellent enantioselectivities. Density functional theory (DFT) studies were carried out to elucidate the origin of the observed enantioselectivity. The importance of the intramolecular N-HO hydrogen-bonding interaction between the sulfonamide and enolate groups was identified to be crucial in inducing a high degree of stereochemical control in both the enolate addition to imine and the subsequent proton transfer step, affording aza-MBH reactions with excellent enantioselectivity.
Authors:
Richmond Lee; Fangrui Zhong; Bin Zheng; Yuezhong Meng; Yixin Lu; Kuo-Wei Huang
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2013-6-17
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  -     ISSN:  1477-0539     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2013 Jun 
Date Detail:
Created Date:  2013-6-18     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Division of Physical Sciences and Engineering and KAUST Catalysis Center, King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi Arabia. hkw@kaust.edu.sa.
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