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General synthesis of P-stereogenic compounds: the menthyl phosphinate approach
Berger, Olivier Montchamp, Jean-Luc
Berger, Olivier
Montchamp, Jean-Luc
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The Royal Society of Chemistry
Date
2016-07-13
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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.
Contents
Subject
Catalyzed dehydrative allylation
asymmetric-synthesis
absolute-configuration
stereospecific reduction
hypophosphorous acid
H-phosphinate
stereocontrolled synthesis
stereoselective-synthesis
diphenylphosphine oxide
chiral phosphorus
asymmetric-synthesis
absolute-configuration
stereospecific reduction
hypophosphorous acid
H-phosphinate
stereocontrolled synthesis
stereoselective-synthesis
diphenylphosphine oxide
chiral phosphorus
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Research Projects
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Description
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Department
Chemistry and Biochemistry