General synthesis of P-stereogenic compounds: the menthyl phosphinate approachShow full item record
Title | General synthesis of P-stereogenic compounds: the menthyl phosphinate approach |
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Author | Berger, Olivier; Montchamp, Jean-Luc |
Date | 2016-07-13 |
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. |
Link | https://doi.org/10.1039/C6OB01413E
https://repository.tcu.edu/handle/116099117/11211 https://pubs.rsc.org/en/Content/ArticleLanding/2016/OB/C6OB01413E |
Department | Chemistry and Biochemistry |
Subject | Catalyzed dehydrative allylation
asymmetric-synthesis absolute-configuration stereospecific reduction hypophosphorous acid H-phosphinate stereocontrolled synthesis stereoselective-synthesis diphenylphosphine oxide chiral phosphorus |
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