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Design of Chiral Bis-Phosphoric Acid Catalyst Derived from (R)-3,3'-Di(2-hydroxy-3-arylphenyl)binaphthol: Catalytic Enantioselective Diels-Alder Reaction of α,β-Unsaturated Aldehydes with Amidodienes.
MedLine Citation:
PMID:  22066907     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Chiral bis-phosphoric acid 1 was designed to identify as a new class of structural features in chiral Brønsted acid catalysts, and evaluated in the Diels-Alder reaction of α,β-unsaturated aldehydes 4 with 1-N-acylamino-1,3-butadienes 3. X-ray diffraction analysis revealed the single atropisomer 1, bearing S axial chirality at 3,3'-biaryl substituents on (R)-binaphthyl and intramolecular hydrogen bonding between the two phosphoric acid moieties. After systematic variation of the catalyst substituents as well as the N-acyl substituents of 1,3-butadiene, the use of an N-Cbz amidodiene 3a in the presence of bis-phosphoric acid 1e with a 2,4,6-tri-isopropylphenyl group was found to be optimal to yield the 1S,6R enantiomeric product 5aa via a Diels-Alder reaction of acrolein (4a). Application of this method to substituted substrates was found to be an efficient ap-proach to the enantioselective synthesis of 3- and 3,6-substituted cyclic formylcarbamates 5. The specific character as well as the utility of 1e was further estab-lished by comparing its enantioselectivity, absolute stereochemistry and catalytic efficiency with that by mono-phosphoric acid 2.
Authors:
Norie Momiyama; Tohru Konno; Yuichi Furiya; Takeaki Iwamoto; Masahiro Terada
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-11-8
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  -     ISSN:  1520-5126     ISO Abbreviation:  -     Publication Date:  2011 Nov 
Date Detail:
Created Date:  2011-11-9     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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