Synthetic utilization of highly stereoselective conjugate addition reactions of phosphorus and sulfur stabilized allylic carbanions

Richard Freeman; Richard K. Haynes; Wendy A. Loughlin; Craig Mitchell; John V. Stokes

doi:10.1351/pac199365040647

Synthetic utilization of highly stereoselective conjugate addition reactions of phosphorus and sulfur stabilized allylic carbanions

Richard Freeman, Richard K. Haynes, Wendy A. Loughlin, Craig Mitchell, John V. Stokes

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Abstract

The completely stereoselective formation of a syn vinylic phosphine oxide from the conjugate addition of lithiated (E)-butenyldiphenyIphosphine oxide to cyclopentenone has been extended to enant-iomerically pure (S)-tert-butyl-(E)-but-2-enylphenylphosphine oxide to provide enantiomerically pure conjugate addition products with cyclic enones. A completely new preparation of the enantiomerically pure phosphine oxide, and exploitation of the conjugate addition reaction of the lithiated reagent with 2-methylcyclopent-2-enone in the synthesis of a vitamin D precursor is described. A novel NMR assay method for determining enantiomeric purity of the phosphine oxide is also described.

Original language	English
Pages (from-to)	647-654
Number of pages	8
Journal	Pure and Applied Chemistry
Volume	65
Issue number	4
DOIs	https://doi.org/10.1351/pac199365040647
Publication status	Published - 01 Jan 1993

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abstract = "The completely stereoselective formation of a syn vinylic phosphine oxide from the conjugate addition of lithiated (E)-butenyldiphenyIphosphine oxide to cyclopentenone has been extended to enant-iomerically pure (S)-tert-butyl-(E)-but-2-enylphenylphosphine oxide to provide enantiomerically pure conjugate addition products with cyclic enones. A completely new preparation of the enantiomerically pure phosphine oxide, and exploitation of the conjugate addition reaction of the lithiated reagent with 2-methylcyclopent-2-enone in the synthesis of a vitamin D precursor is described. A novel NMR assay method for determining enantiomeric purity of the phosphine oxide is also described.",

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T1 - Synthetic utilization of highly stereoselective conjugate addition reactions of phosphorus and sulfur stabilized allylic carbanions

AU - Freeman, Richard

AU - Haynes, Richard K.

AU - Loughlin, Wendy A.

AU - Mitchell, Craig

AU - Stokes, John V.

PY - 1993/1/1

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N2 - The completely stereoselective formation of a syn vinylic phosphine oxide from the conjugate addition of lithiated (E)-butenyldiphenyIphosphine oxide to cyclopentenone has been extended to enant-iomerically pure (S)-tert-butyl-(E)-but-2-enylphenylphosphine oxide to provide enantiomerically pure conjugate addition products with cyclic enones. A completely new preparation of the enantiomerically pure phosphine oxide, and exploitation of the conjugate addition reaction of the lithiated reagent with 2-methylcyclopent-2-enone in the synthesis of a vitamin D precursor is described. A novel NMR assay method for determining enantiomeric purity of the phosphine oxide is also described.

AB - The completely stereoselective formation of a syn vinylic phosphine oxide from the conjugate addition of lithiated (E)-butenyldiphenyIphosphine oxide to cyclopentenone has been extended to enant-iomerically pure (S)-tert-butyl-(E)-but-2-enylphenylphosphine oxide to provide enantiomerically pure conjugate addition products with cyclic enones. A completely new preparation of the enantiomerically pure phosphine oxide, and exploitation of the conjugate addition reaction of the lithiated reagent with 2-methylcyclopent-2-enone in the synthesis of a vitamin D precursor is described. A novel NMR assay method for determining enantiomeric purity of the phosphine oxide is also described.

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Synthetic utilization of highly stereoselective conjugate addition reactions of phosphorus and sulfur stabilized allylic carbanions

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