Cyclic Phosphine Oxides and Phosphinamides from Di-Grignard Reagents and Phosphonic Dichlorides: Modular Access to Annulated Phospholanes

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• 作者：Aaron M. Gregson ; Steven M. Wales ; Stephen J. Bailey ; Anthony C. Willis ; Paul A. Keller
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：October 2, 2015
• 年：2015
• 卷：80
• 期：19
• 页码：9774-9780
• 全文大小：469K
• ISSN：1520-6904

文摘

The reaction between 1,4-di-Grignard reagents and phosphonous(III) dichlorides is a classical method for the direct synthesis of phospholanes. Reported here is an extension of this approach to the preparation of value-added, annulated phospholane oxides, achieved through the combination of carbocyclic-fused di-Grignard reagents and readily available phosphonic(V) dichlorides. The procedure is amenable to (benz)annulation at both the 2,3- and 3,4-positions of the phospholane ring, and a variety of aliphatic, cyclic and aryl P-electrophiles are tolerated in reasonable to excellent yields.