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

Aaron M. Gregson; Steven M. Wales; Stephen J. Bailey; Anthony C. Willis; Paul A. Keller

doi:10.1021/acs.joc.5b01476

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

Aaron M. Gregson, Steven M. Wales, Stephen J. Bailey, Anthony C. Willis, Paul A. Keller^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

11 Citations (SciVal)

Abstract

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.

Original language	English
Pages (from-to)	9774-9780
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	80
Issue number	19
DOIs	https://doi.org/10.1021/acs.joc.5b01476
Publication status	Published - 2 Oct 2015

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

abstract = "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.",

author = "Gregson, {Aaron M.} and Wales, {Steven M.} and Bailey, {Stephen J.} and Willis, {Anthony C.} and Keller, {Paul A.}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

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T1 - Cyclic Phosphine Oxides and Phosphinamides from Di-Grignard Reagents and Phosphonic Dichlorides

T2 - Modular Access to Annulated Phospholanes

AU - Gregson, Aaron M.

AU - Wales, Steven M.

AU - Bailey, Stephen J.

AU - Willis, Anthony C.

AU - Keller, Paul A.

PY - 2015/10/2

Y1 - 2015/10/2

N2 - 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.

AB - 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.

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U2 - 10.1021/acs.joc.5b01476

DO - 10.1021/acs.joc.5b01476

M3 - Article

SN - 0022-3263

VL - 80

SP - 9774

EP - 9780

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

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

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