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

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

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

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
Publication status	Published - 1 Jan 1993
Externally published	Yes

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title = "Synthetic utilization of highly stereoselective conjugate addition reactions of phosphorus and sulfur stabilized allylic carbanions",

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.",

author = "Richard Freeman and Haynes, \{Richard K.\} and Loughlin, \{Wendy A.\} and Craig Mitchell and Stokes, \{John V.\}",

year = "1993",

month = jan,

day = "1",

language = "English",

volume = "65",

pages = "647--654",

journal = "Pure and Applied Chemistry",

issn = "0033-4545",

publisher = "Walter de Gruyter GmbH",

number = "4",

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TY - JOUR

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

Y1 - 1993/1/1

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.

UR - https://www.scopus.com/pages/publications/0000568782

M3 - Journal Article

SN - 0033-4545

VL - 65

SP - 647

EP - 654

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

IS - 4

ER -

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

Abstract

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