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The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.50777-76-9, Name is 2-(Diphenylphosphino)benzaldehyde, molecular formula is C19H15OP. In a Article£¬once mentioned of 50777-76-9, Safety of 2-(Diphenylphosphino)benzaldehyde

<1N,3E>-Bifunctional Phosphorodiamidites and the Diastereoselective Phosphonylation of Aldehydes. Controlling, Elucidating and Rationalising the Stereochemical Course of the Asymmetric Abramov Reaction

The novel, chiral phosphorodiamidite <(1R,2S)-O,N-ephedrine>PN(SiMe3)2 2 has been prepared cleanly in both high chemical (83percent) and epimeric (>98percent) yields from the reaction of LiN(SiMe3)2 with <(1R,2S)-O,N-ephedrine>PCl 1.The configuration at phosphorus has been shown to be SP by a combination of NMR and derivatisation studies.Phosphorodiamidite 2 phosphonylates aldehydes (RCHO) readily via the Abramov reaction to afford alpha-siloxyimidophosphonate esters of the form <(1R,2S)-O,N-ephedrine>P(NSiMe3)CHR(OSiMe3) (R = alkyl and substituted phenyl) with diastereoselectivities up to 96percent (for R = t-Bu).In each case, NMR spectroscopy reveals that both major and minor product esters have the SP configuration supportive of the Abramov reaction proceeding with retention of configuration at phosphorus and this is supported by X-ray diffraction studies on alpha-siloxyimidophosphonate esters with R = 2-naphthyl 9 and 2-Ph2PC6H4 11.Subsequently, an empirical method od assigning configurations to both the phosphorus and alpha-carbon atoms is proposed on the basis of 1H and 31P NMR measurements.Experiments also suggest that the Abramov reaction (i) is subject to kinetic contril under the conditions reported here but can be reversed under more forcing thermal conditions or in the presence of trace acid, (ii) involves intramolecular transfer of ther triorganosilyl group, (iii) involves significant bond formation in the rate-determing step, (iv) probably does not proceed via pre-coordination of the carbonyl oxygen atom to silicon (by 29Si<1H> NMR) in contrast to metallophosphite systems and (v) the configuration at the alpha-carbon stereocentre is controlled primarily by steric rather than distal electronic factors in systems where R = XC6H4.Consequently, steric interactions in the rate-determining transition state may account for the reversal in face-selectivity in the reactions between compound 2 and 2-C10H7CHO, for which the major product isomer 9 has the (SP,SC) configuration, and 2 and 2-Ph2PC6H4CHO, for which the major product isomer 11 has the (SP,RC) configuration.

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Reference£º
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate