Asymmetric synthesis and the novel retro Diels-Alder reaction of a P-chiral sulfonyl-substituted phosphanorbornene

An asymmetric Diels-Alder reaction between phenylvinylsulfone and 1-phenyl-3,4-dimethylphosphole in the presence of a chiral organometallic reaction promoter generates the corresponding P-chiral sulfonyl-substituted phosphanorbornene which is found to undergo the facile cycloreversion reaction under mild conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.