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Issue 31, 2016
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General synthesis of P-stereogenic compounds: the menthyl phosphinate approach

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Abstract

Easily prepared menthyl phosphinates of high diastereoisomeric purity provide versatile intermediates for the synthesis of P-stereogenic compounds. Previous efforts starting about fifty years ago have been hampered by a lack of generality so the menthyl route has been nearly abandoned. Herein we provide a general solution to this long-standing problem and describe a general synthesis of menthyl H-phosphinate and disubstituted phosphinate esters. The method to prepare these versatile precursors relies on a simple and inexpensive process avoiding the use of phosphorus trichloride, Grignard reagents, and complicated cryogenic crystallizations. Established protocols can then be employed to synthesize P-stereogenic secondary and tertiary phosphine oxides and therefore P-stereogenic phosphine ligands.

Graphical abstract: General synthesis of P-stereogenic compounds: the menthyl phosphinate approach

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Publication details

The article was received on 30 Jun 2016, accepted on 13 Jul 2016 and first published on 13 Jul 2016


Article type: Paper
DOI: 10.1039/C6OB01413E
Citation: Org. Biomol. Chem., 2016,14, 7552-7562
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    General synthesis of P-stereogenic compounds: the menthyl phosphinate approach

    O. Berger and J. Montchamp, Org. Biomol. Chem., 2016, 14, 7552
    DOI: 10.1039/C6OB01413E

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