Phosphine-mediated [4 + 2] annulation of bis(enones): a Lewis base catalyzed "mock Diels-Alder" reaction.
Lewis-base-catalyzed cycloisomerization of bis(enones) to decalins has been demonstrated as an alternative to the traditional Lewis acid catalyzed Diels-Alder cycloaddition. In this process, a trialkylphosphine mediates both bond formation steps in two distinct catalytic cycles. The single-pot operation generates two carbon-carbon bonds and up to five contiguous stereocenters in one step, starting from achiral, aliphatic substrates; eight examples are provided. [reaction: see text]
Couturier
Michel
M
Chemical Research and Development, Pfizer Global Research and Development, Eastern Point Road, P.O. Box 8013, Groton, CT 06340-8013, USA. michel_a_couturier@groton.pfizer.com
Ménard
Fréderic
F
Ragan
John A
JA
Riou
Maxime
M
Dauphin
Etienne
E
Andresen
Brian M
BM
Ghosh
Arun
A
Dupont-Gaudet
Kristina
K
Girardin
Mélina
M