Synthesis of 2, 3-dihydro-1-phenylbenzo [b] phosphole (1-phenylphosphindane) and its use as a mechanistic test in the asymmetric Appel reaction: decisive evidence …

DJ Carr, JS Kudavalli, KS Dunne…

Index: Carr, Damien J.; Kudavalli, Jaya Satyanarayana; Dunne, Katherine S.; Mueller-Bunz, Helge; Gilheany, Declan G. Journal of Organic Chemistry, 2013 , vol. 78, # 20 p. 10500 - 10505

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Citation Number: 12

Abstract

Racemic 2, 3-dihydro-1-phenylbenzo [b] phosphole was obtained by reduction of 1- phenylbenzo [b] phosphole-1-oxide, itself derived by ring-closing metathesis of phenylstyrylvinylphosphine oxide. The title compound was then reoxidized under asymmetric Appel conditions. Comparison of the sense and degree of the stereoselectivity to those obtained with an open-chain analogue indicated that the ring system does not affect ...