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New chiral scandium(III)/bisimine and diol complexes catalyzed asymmetric Diels–Alder reaction

✍ Scribed by Shin-ichi Fukuzawa; Yoshitaka Komuro; Narihito Nakano; Shinya Obara

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
81 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

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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