New chiral scandium(III)/bisimine and diol complexes catalyzed asymmetric Diels-Alder reaction |
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Authors: | Shin-ichi Fukuzawa Yoshitaka KomuroNarihito Nakano Shinya Obara |
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Institution: | Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan |
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Abstract: | Several bisimine and diol-based chiral ligands were examined as scandium(III) triflate complexes in the asymmetric Diels-Alder reaction of cyclopentadiene (2) with 3-acryloyloxazolidin-2-one (1) in the presence of 2,6-lutidine: the scandium/salen complex was revealed to be the most effective catalyst, which afforded the endo adduct in a good yield with 85% ee. Addition of a tertiary amine, such as 2,6-lutidine, was critical to achieve high enantioselectivity; enantioselectivity was remarkably decreased in the absence of the amine. |
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