138442-64-5

Upstream product

• 65838-10-0 (1R,2R)-N,N'-dibenzylcyclohexane-1,2-diamine 
• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 100-52-7 benzaldehyde 
• 32044-22-7 (R,R)-1,2-diaminocyclohexane*(+)-tartric acid 
• 138421-30-4 (3aR,7aR)-1,3-Dibenzyl-2-triethylsilanyloxy-octahydro-benzo[1,3,2]diazaphosphole 
• 138421-25-7 (1R,5R)-3-chloro-2,4-dibenzyl-2,4-diaza-3-phosphabicyclo[3.4.0]nonane 

Downstream Products

• 138421-35-9 (3aR,7aR)-1,3-Dibenzyl-2-methyl-octahydro-benzo[1,3,2]diazaphosphole 2-oxide 
• 368887-07-4 2-chloro-2,3,3a,4,5,6,7,7a-octahydro-1,3-bis(phenylmethyl)-1H-1,3,2-benzodiazaphosphole-2-oxide 
• 138421-38-2 (3aR,7aR)-2-Allyl-1,3-dibenzyl-octahydro-benzo[1,3,2]diazaphosphole 2-oxide 
• 138421-36-0 (3aR,7aR)-octahydro-1,2,3-tribenzyl-1,3,2-benzodiazaphosphole 2-oxide 

Relevant academic research and scientific papers

Synthesis of new sulfonium ylides bearing the chiral diazaphospholidine group as reagents for asymmetric cyclopropanation

Sulfonium ylides derived from chiral N,N′-substituted (benzyl, isopropyl, neopentyl) phosphonamides were prepared by reacting appropriate chiral diamidophosphites with potassium hydride and chloromethyl methyl sulfide, and then with methyl iodide in the presence AgBF4 to give the corresponding sulfonium salts in high yields. One of them was analyzed by X-ray crystallography. The salts upon treatment with different bases (LithiumDiisopropylAmine, BuLi, K2CO3) were converted in situ into ylides, which were reacted with activated olefins to produce phosphonocyclopropanes as a mixture of two diastereoisomers with moderate-to-high diastereoselectivities.

The synthesis, structure and properties of diazaphospholes: Reagents and ligands for asymmetric synthesis

Reaction of C2 diamines with PCl3 and Et3N in toluene, followed by water or hydrogen sulfide, gave a series of cyclic phosphorous acid diamides (diazaphosphole oxides) and thiophosphorous acid diamides (diazaphosphole sulf

REACTIONS OF CHIRAL PHOSPHOROUS ACID DIAMIDES

Chiral phosphorous acid diamides were prepared from chiral C2 diamines via the sequential addition of PCl3 and H2O.Alternatively, addition of PCl3 and hydrogen sulfide yielded the analogous thiophosphorous acid diamides.Deprotonation of the phosphorous acids under a variety of conditions gave the anions which reacted smoothly with alkyl halides to give phosphonamides in good yield.Reaction of the anions with aldehydes gave α-hydroxy-phosphonamides in good yield and with modest diastereoselectivity (1:1 - 25:1 ds).Treatment of the phosphorous acids with trialkylsilyl triflates and Hunnig's base gave the product of O-silylation.

The Preparation and Reactions of Chiral Phosphorous Acid Diamides

Chiral phosphorous acid diamides were prepared by condensation of N,N'-disubstituted C2 diamines with PCl3 followed by an equivalent of water.Deprotonation of these acids with n-butyl lithium or LDA gave the lithium salt which reacted smoothly with alkyl halides to give the substituted phosphonamides in good yield. Key Words: phosphorous acid; chiral; phosphonamide; alkylation; diamine.