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New chiral sulfoxide ligands in catalytic asymmetric Diels–Alder reactions: double acceleration by the chiralities of the sulfoxides and oxazolines

✍ Scribed by Kunio Hiroi; Kazuhiro Watanabe; Ikuko Abe; Michiko Koseki

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 64 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01646-x

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✦ Synopsis

New chiral sulfoxide ligands which are useful for catalytic asymmetric Diels-Alder reactions have been developed. The new ligands involve a chiral sulfinyl function and a 1,3-oxazoline ring with an asymmetric carbon center, in which the chiral sulfinyl group has been revealed to play a crucial role in achieving high enantioselectivity in asymmetric Diels-Alder reactions. Among the Lewis acid catalysts employed, magnesium iodide provided the highest chemical and stereochemical efficiency in the cycloaddition reactions. A mechanistic pathway for the asymmetric synthesis is proposed on the basis of the stereochemical outcomes obtained.

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