Rational design of a new chiral Lewis acid catalyst for enantioselective Diels-Alder reaction: Optically active 2-dichloroboryl-1,1 '-binaphthyl

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 alpha,beta-unsaturated esters, and could be reused as the corresponding boronic acid. In addition, a new convenient method f...

Full description

Saved in:
Bibliographic Details
Published inSynlett no. 10; pp. 1053 - 1057
Main Authors Ishihara, K, Inanaga, K, Kondo, S, Funahashi, M, Yamamoto, H
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.10.1998
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
enantioselective Diels-Alder reaction
CINNAMIC ESTERS
chiral Lewis acid catalyst
2-dichloroboryl-1
alpha,beta-unsaturated ester
SYSTEMS
ALDEHYDES
CYCLOPENTADIENE
PHOTOCHEMICAL-REACTIONS
1 '-binaphthyl
chiral arylboronic acid
Online AccessGet more information

Cover

More Information
Summary: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 alpha,beta-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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-1998-1860