dc.creator | Berger, Olivier | |
dc.creator | Montchamp, Jean-Luc | |
dc.date.accessioned | 2016-08-03T21:49:53Z | |
dc.date.available | 2016-08-03T21:49:53Z | |
dc.date.issued | 2016-07-13 | |
dc.identifier.uri | https://doi.org/10.1039/C6OB01413E | |
dc.identifier.uri | https://repository.tcu.edu/handle/116099117/11211 | |
dc.identifier.uri | https://pubs.rsc.org/en/Content/ArticleLanding/2016/OB/C6OB01413E | |
dc.description.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. | |
dc.language.iso | en | en_US |
dc.publisher | The Royal Society of Chemistry | |
dc.rights.uri | https://creativecommons.org/licenses/by/3.0/ | |
dc.source | Organic & Biomolecular Chemistry | |
dc.subject | Catalyzed dehydrative allylation | |
dc.subject | asymmetric-synthesis | |
dc.subject | absolute-configuration | |
dc.subject | stereospecific reduction | |
dc.subject | hypophosphorous acid | |
dc.subject | H-phosphinate | |
dc.subject | stereocontrolled synthesis | |
dc.subject | stereoselective-synthesis | |
dc.subject | diphenylphosphine oxide | |
dc.subject | chiral phosphorus | |
dc.title | General synthesis of P-stereogenic compounds: the menthyl phosphinate approach | |
dc.type | Article | |
dc.rights.holder | Berger et al. | |
dc.rights.license | CC BY 3.0 | |
local.college | College of Science and Engineering | |
local.department | Chemistry and Biochemistry | |
local.persons | All (CHEM) | |