1354049-99-2

Upstream product

• 1257102-84-3 (4-fluoro-2-methylphenyl)(methyl)phenylphosphane 
• 1354049-89-0 methylphenyl-(2-methyl-4-fluorophenyl) phosphonium chloride 
• 1257102-90-1 (+/-)-(4-fluoro-2-methylphenyl)methylphenylphosphine oxide 

Relevant academic research and scientific papers

Lithium Borohydride for Achiral and Stereospecific Reductive Boronation at Phosphorus: Lack of Electronic Effects on Stereoselective Formation of Alkoxyphosphonium Salts

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.

Identification of a key intermediate in the asymmetric Appel process: One pot stereoselective synthesis of P-stereogenic phosphines and phosphine boranes from racemic phosphine oxides

Sequential treatment of racemic phosphine oxides with oxalyl chloride and chiral non-racemic alcohol generates the same ratios of diastereomeric alkoxyphosphonium salts obtained in the corresponding asymmetric Appel process, strongly implicating the intermediate chlorophosphonium salt in the stereoselecting step. Subsequent reduction allows a novel synthesis of enantioenriched P-stereogenic phosphines-phosphine boranes. The Royal Society of Chemistry 2012.

A U-turn in the asymmetric appel reaction: Stereospecific reduction of diastereomerically enriched alkoxyphosphonium salts allows the asymmetric synthesis of P-stereogenic phosphanes and phosphane boranes

An efficient one-pot synthesis has been developed of enantioenriched P-stereogenic phosphanes and phosphane boranes from the corresponding racemic phosphanes in excellent yield under asymmetric Appel conditions. The chiral auxiliary (menthol) can also be recovered unchanged. The simple and efficient protocol significantly expands the scope of our asymmetric Appel process. The crucial step in the preparation involves stereospecific reduction of intermediate diastereomeric alkoxyphosphonium salts, which are obtained in the reaction of phosphane, hexachloroacetone, and menthol. Thereby, reaction with LiAlH4 or NaBH4 gives the corresponding phosphanes or phosphane boranes, respectively. Copyright

PROCESSES FOR THE STEREOSELECTIVE PREPARATION OF P-CHIRAL FOUR -COORDINATED PHOSPHORUS BORANE COMPOUNDS AND P-CHIRAL THREE-COORDINATED PHOSPHORUS COMPOUNDS

Processes for the stereoselective preparation of P-chiral four-coordinated phosphorus borane compounds and P-chiral three-coordinated phosphorus compounds.

Simple unprecedented conversion of phosphine oxides and sulfides to phosphine boranes using sodium borohydride

A variety of phosphine oxides and sulfides can be efficiently converted directly to the corresponding phosphine boranes using oxalyl chloride followed by sodium borohydride. Optically active P-stereogenic phosphine oxides can be converted stereospecifically to phosphine boranes with inversion of configuration by treatment with Meerwein's salt followed by sodium borohydride.