Stereocontrolled route to some optically active β-hydroxy phosphine oxides using the stereoselective addition of metallated phosphine oxides to proline-derived keto aminals

DOI: 10.1039/P19960002117

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2117 - 2127 (1996)

Update date:2022-08-03

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Authors:

O'Brien, Peter

Warren, Stuart

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Article abstract of DOI:10.1039/P19960002117

An asymmetric Horner-Wittig addition reaction with a chiral auxiliary attached to the electrophile is described. The key step is the addition of metallated phosphine oxides to Mukaiyama's proline-derived keto aminals (for which improved syntheses are described) and a detailed study of the factors affecting the stereoselectivity of these reactions is presented. In particular, by suitable choice of metallation conditions, complementary stereoselectivities are observed: reactions in THF with no additives are syn selective (Felkin non-chelation control) whereas reactions in toluene with added lithium bromide are anti selective (Cram chelation control).

Full text of DOI:10.1039/P19960002117

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