129212-59-5Relevant articles and documents
Stereochemistry of palladium-mediated synthesis of PAMP-BH3: Retention of configuration at P in formation of Pd-P and P-C bonds
Moncarz, Jillian R.,Brunker, Tim J.,Glueck, David S.,Sommer, Roger D.,Rheingold, Arnold L.
, p. 1180 - 1181 (2003)
Treatment of Pd((S,S)-Chiraphos)(o-An)(I) (3, o-An = o-MeOC6H4) with either enantiomer of highly enantioenriched PH(Me)(Ph)(BH3) (1) gave the phosphido-borane complex Pd((S,S)-Chiraphos)(o-An)(P(Me)(Ph)(BH3)) (4
Iridium-catalyzed enantioselective C-H borylation of diarylphosphinates
Song, Shu-Yong,Li, Yinwu,Ke, Zhuofeng,Xu, Senmiao
, p. 13445 - 13451 (2021/11/16)
P-stereogenic phosphorus compounds are a ubiquitous and critically important class of chiral ligands in asymmetric catalysis. Methods for catalytic asymmetric synthesis via a step- and atom-economic way are still very limited. We herein disclose a protocol of phosphinate-directed iridium-catalyzed enantioselective ortho-H borylation to construct P-stereogenic phosphorus compounds. A number of functional groups could be well tolerated to afford optically active diarylphosphinates with good to excellent enantioselectivities (up to 92% ee). We also demonstrate the synthetic utilities of the obtained borylated products, including the synthesis of precursors for chiral phosphine ligands.
Lithium Borohydride for Achiral and Stereospecific Reductive Boronation at Phosphorus: Lack of Electronic Effects on Stereoselective Formation of Alkoxyphosphonium Salts
Al Sulaimi, Sulaiman S.,Rajendran, Kamalraj V.,Gilheany, Declan G.
supporting information, p. 5959 - 5965 (2015/09/22)
We report LiBH4 as a preferred, simple and effective reagent for reductive boronation of achiral and racemic chlorophosphonium salts (CPS) and for diastereomeric alkoxyphosphonium salts (DAPS), both of which are, in turn, easily generated from either the corresponding phosphane or, more conveniently, the phosphane oxide. Further, we have shown that the DAPS reduction/boronation could be achieved with complete stereocontrol to give scalemic phosphane-borane directly in excellent yield and enantiomeric excess (ee). This new methodology was employed to investigate the effects of aryl substitution on the outcome of dynamic kinetic resolution of arylmethylphenylphosphanes and phosphane oxides via DAPS. It was found that substitution at the ortho position strongly affects the degree of stereoselection. However, surprisingly, we confirmed that there was no variation of stereoselectivity seen with the electronic effect of substituents on the para position.
