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dc.creatorBerger, Olivier
dc.creatorMontchamp, Jean-Luc
dc.date.accessioned2016-08-03T21:49:53Z
dc.date.available2016-08-03T21:49:53Z
dc.date.issued2016-07-13
dc.identifier.urihttps://doi.org/10.1039/C6OB01413E
dc.identifier.urihttps://repository.tcu.edu/handle/116099117/11211
dc.identifier.urihttps://pubs.rsc.org/en/Content/ArticleLanding/2016/OB/C6OB01413E
dc.description.abstractEasily 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.
dc.language.isoenen_US
dc.publisherThe Royal Society of Chemistry
dc.rights.urihttps://creativecommons.org/licenses/by/3.0/
dc.sourceOrganic & Biomolecular Chemistry
dc.subjectCatalyzed dehydrative allylation
dc.subjectasymmetric-synthesis
dc.subjectabsolute-configuration
dc.subjectstereospecific reduction
dc.subjecthypophosphorous acid
dc.subjectH-phosphinate
dc.subjectstereocontrolled synthesis
dc.subjectstereoselective-synthesis
dc.subjectdiphenylphosphine oxide
dc.subjectchiral phosphorus
dc.titleGeneral synthesis of P-stereogenic compounds: the menthyl phosphinate approach
dc.typeArticle
dc.rights.holderBerger et al.
dc.rights.licenseCC BY 3.0
local.collegeCollege of Science and Engineering
local.departmentChemistry and Biochemistry
local.personsAll (CHEM)


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