Preparation of Enantiomerically Pure Tertiary Phosphine Oxides from, and Assay of Enantiomeric Purity with, (Rp)- and (Sp)-tert-Butylphenylphosphinothioic Acids

Richard K. Haynes; Richard N. Freeman; Craig R. Mitchell; Simone C. Vonwiller

doi:10.1021/jo00090a003

Preparation of Enantiomerically Pure Tertiary Phosphine Oxides from, and Assay of Enantiomeric Purity with, (R_p)- and (S_p)-tert-Butylphenylphosphinothioic Acids

Richard K. Haynes, Richard N. Freeman, Craig R. Mitchell, Simone C. Vonwiller

The University of Sydney

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

61 Citations (Scopus)

Abstract

A convenient multigram scale method has been developed for preparation of enantiomerically-pure (R_p)- and (S_p)-tertiary phosphine oxides including allyl- and but-2-enyl-tert-butylphenylphosphine oxides wherein (R_p)- and (S_p)-tert-butyl-phenylphosphinothioic acids are converted into (R_p)- and (S_p)-tert-butylphenylphosphine oxides by ultrasound irradiation in the presence of Raney-Ni at room temperature and the secondary phosphine oxides then metalated and treated with alkyl halides.

Original language	English
Pages (from-to)	2919-2921
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	59
Issue number	11
DOIs	https://doi.org/10.1021/jo00090a003
Publication status	Published - 01 Jun 1994

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10.1021/jo00090a003

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title = "Preparation of Enantiomerically Pure Tertiary Phosphine Oxides from, and Assay of Enantiomeric Purity with, (Rp)- and (Sp)-tert-Butylphenylphosphinothioic Acids",

abstract = "A convenient multigram scale method has been developed for preparation of enantiomerically-pure (Rp)- and (Sp)-tertiary phosphine oxides including allyl- and but-2-enyl-tert-butylphenylphosphine oxides wherein (Rp)- and (Sp)-tert-butyl-phenylphosphinothioic acids are converted into (Rp)- and (Sp)-tert-butylphenylphosphine oxides by ultrasound irradiation in the presence of Raney-Ni at room temperature and the secondary phosphine oxides then metalated and treated with alkyl halides.",

author = "Haynes, {Richard K.} and Freeman, {Richard N.} and Mitchell, {Craig R.} and Vonwiller, {Simone C.}",

year = "1994",

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pages = "2919--2921",

journal = "Journal of Organic Chemistry",

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Preparation of Enantiomerically Pure Tertiary Phosphine Oxides from, and Assay of Enantiomeric Purity with, (R_p)- and (S_p)-tert-Butylphenylphosphinothioic Acids. / Haynes, Richard K.; Freeman, Richard N.; Mitchell, Craig R. et al.
In: Journal of Organic Chemistry, Vol. 59, No. 11, 01.06.1994, p. 2919-2921.

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

TY - JOUR

T1 - Preparation of Enantiomerically Pure Tertiary Phosphine Oxides from, and Assay of Enantiomeric Purity with, (Rp)- and (Sp)-tert-Butylphenylphosphinothioic Acids

AU - Haynes, Richard K.

AU - Freeman, Richard N.

AU - Mitchell, Craig R.

AU - Vonwiller, Simone C.

PY - 1994/6/1

Y1 - 1994/6/1

N2 - A convenient multigram scale method has been developed for preparation of enantiomerically-pure (Rp)- and (Sp)-tertiary phosphine oxides including allyl- and but-2-enyl-tert-butylphenylphosphine oxides wherein (Rp)- and (Sp)-tert-butyl-phenylphosphinothioic acids are converted into (Rp)- and (Sp)-tert-butylphenylphosphine oxides by ultrasound irradiation in the presence of Raney-Ni at room temperature and the secondary phosphine oxides then metalated and treated with alkyl halides.

AB - A convenient multigram scale method has been developed for preparation of enantiomerically-pure (Rp)- and (Sp)-tertiary phosphine oxides including allyl- and but-2-enyl-tert-butylphenylphosphine oxides wherein (Rp)- and (Sp)-tert-butyl-phenylphosphinothioic acids are converted into (Rp)- and (Sp)-tert-butylphenylphosphine oxides by ultrasound irradiation in the presence of Raney-Ni at room temperature and the secondary phosphine oxides then metalated and treated with alkyl halides.

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Preparation of Enantiomerically Pure Tertiary Phosphine Oxides from, and Assay of Enantiomeric Purity with, (R_p)- and (S_p)-tert-Butylphenylphosphinothioic Acids

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