The Lewis acid-catalyzed intramolecular asymmetric ene reaction using a chiral α-cyanovinylic sulfoxide as an enophile

DOI: 10.1016/S0040-4020(01)80539-1

Source and publish data:

Tetrahedron p. 1831 - 1840 (1993)

Update date:2022-08-04

Topics:

Authors:

Hiroi, Kunio

Umemura, Masayuki

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Article abstract of DOI:10.1016/S0040-4020(01)80539-1

A chiral α-cyanovinylic sulfoxide served as an efficient chiral enophile in a Lewis acid-catalyzed intramolecular ene reaction. Use of diethylaluminum chloride as a catalyst provided extremely high stereoselectivity in the ene reaction. The stereochemistry of the ene reaction products were determined by chemical correlation and the NMR spectral analysis. A mechanistic pathway for the asymmetric induction is presented on the basis of the stereochemical results obtained.

Full text of DOI:10.1016/S0040-4020(01)80539-1

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