Tetrahedron p. 8941 - 8962 (1997)
Update date:2022-07-30
Topics:
Boeckman Jr., Robert K.
Breining, Scott R.
Arvanitis, Argyrios
A tandem cyclopropyliminium ion rearrangement-Hofmann elimination affords rapid access to 3-vinyl Δ2-pyrrolines in some cases bearing an unsaturated tether in good yield. The resulting dienamines subsequently undergo both inter-and intramolecular [4+2] cycloaddition reactions. Good yields were obtained for a number of cases of intramolecular intermolecular cycloaddition reactions affording cycloadducts in good yields with sufficiently reactive dienophiles such as fumarate, acrylate and methacrolein. Evidence suggests a non-concerted pathway for these cycloaddition reactions.
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