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 against Involvement of Pseudorota

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• 作者：Damien J. Carr ; Jaya Satyanarayana Kudavalli ; Katherine S. Dunne ; Helge M眉ller-Bunz ; Declan G. Gilheany
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：October 18, 2013
• 年：2013
• 卷：78
• 期：20
• 页码：10500-10505
• 全文大小：278K
• 年卷期：v.78,no.20(October 18, 2013)
• ISSN：1520-6904

文摘

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 the selectivity of the process. This in turn strongly suggests that the stereoselection is not related to pseudorotamer preferences in putative phosphorane intermediates.