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Synlett 1998; 1998(10): 1053-1056
DOI: 10.1055/s-1998-1860
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Rational Design of a New Chiral Lewis Acid Catalyst for Enantioselective Diels-Alder Reaction: Optically Active 2-Dichloroboryl-1,1′-binaphthyl

Kazuaki Ishihara* , Kazato Inanaga, Shoichi Kondo, Miyuki Funahashi, Hisashi Yamamoto
  • *Research Center for Advanced Waste and Emission Management (ResCWE), Nagoya University, CREST, Japan Science and Technology Corporation (JST), Furo-cho, Chikusa, Nagoya 464-8603, Japan; Fax 81-52-789-3222
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Publication Date:
31 December 2000 (online)

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A novel chiral aryldichloroborane catalyst bearing binaphthyl skeletons with axial chirality was developed as an asymmetric catalyst for the Diels-Alder reaction of dienes and α,β-unsaturated esters, and could be reused as the corresponding boronic acid. In addition, a new convenient method for preparing arylboronic acids from aryl alcohols is described.

enantioselective Diels-Alder reaction - chiral Lewis acid catalyst - α,β-unsaturated ester - 2-dichloroboryl-1,1′-binaphthyl - chiral arylboronic acid

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