Hetero-Diels–Alder Reaction of Phosphinyl and Phosphonyl Nitroso Alkenes with Conjugated Dienes: An Aza-Cope Rearrangement

JM de los Santos, R Ignacio, G Rubiales…

Index: De Los Santos, Jesus M.; Ignacio, Roberto; Rubiales, Gloria; Aparicio, Domitila; Palacios, Francisco Journal of Organic Chemistry, 2011 , vol. 76, # 16 p. 6715 - 6725

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Citation Number: 14

Abstract

Phosphorylated nitroso alkenes react with cyclic dienes such as cyclopentadiene or cyclohexadiene to afford hetero Diels–Alder-type cycloadducts where the nitroso alkene participates as dienophile component and the cyclic olefin acts as the 4π-electron (diene) system. Subsequent aza-Cope rearrangement affords highly functionalized 5, 6-dihydro-4 H- 1, 2-oxazines. Conversely, the reaction of TMS-substituted cyclopentadiene (dienophile) ...