General synthesis of P-stereogenic compounds: the menthyl phosphinate approachShow full item record
|Title||General synthesis of P-stereogenic compounds: the menthyl phosphinate approach|
|Author||Berger, Olivier; Montchamp, Jean-Luc|
|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.|
|Department||Chemistry and Biochemistry|
|Subject||Catalyzed dehydrative allylation
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