1357013-33-2

Upstream product

• 105198-76-3 5-(tert-Butyl-diphenyl-silanyloxy)-1-trimethylsilanyl-pent-1-yn-3-one 
• 225114-80-7 5-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyl-pent-1-yn-3-ol 
• 90-05-1 2-methoxy-phenol 
• 613-70-7 2-methoxyphenyl acetate 
• 66037-04-5 1-acetoxy-5-bromo-2-methoxybenzene 
• 37942-01-1 5-bromo-2-methoxyphenol 
• 138509-45-2 4-bromo-2-cyclopentyloxyanisole 
• 536-74-3 phenylacetylene 
• 1357013-32-1 (R)-tert-butyl((3-(3-(cyclopentyloxy)-4-methoxyphenyl)-5-phenylpent-4-yn-1-yl)oxy)dimethylsilane 
• 1357013-17-2 5-((tert-butyldimethylsilyl)oxy)-1-phenylpent-1-yn-3-yl (2,4,6-trimethoxyphenyl)carbonate 

Relevant academic research and scientific papers

Synthesis of a TNF inhibitor, flurbiprofen and an: I -Pr analogue in enantioenriched forms by copper-catalyzed propargylic substitution with Grignard reagents

The copper-catalyzed substitution reaction of diethyl phosphate derived from TMSCCCH(OH)CH2CH2OTBDPS with 3-c-C5H9-4-MeOC6H3MgBr, followed by several transformations, afforded a tumor necrosis factor inhibitor possessing a Ph-acetylene moiety. The inhibitor was also synthesized from phenylacetylene phosphate PhCCCH(OP(O)(OEt)2)CH2CH2OTBDPS. Furthermore, the substitution of phosphates derived from TMSCCCH(OH)CH3 and TMSCCCH(OH)-i-Pr with 3-F-4-PhC6H3MgBr gave the corresponding substitution products, which were transformed to flurbiprofen and its i-Pr analogue, respectively. The copper-catalyzed substitutions in these syntheses proceeded in a regio- and stereoselective manner. This journal is

Nickel-catalyzed enantioselective cross-couplings of racemic secondary electrophiles that bear an oxygen leaving group

To date, effective nickel-catalyzed enantioselective cross-couplings of alkyl electrophiles that bear oxygen leaving groups have been limited to reactions of allylic alcohol derivatives with Grignard reagents. In this Communication, we establish that, in the presence of a nickel/pybox catalyst, a variety of racemic propargylic carbonates are suitable partners for asymmetric couplings with organozinc reagents. The method is compatible with an array of functional groups and utilizes commercially available catalyst components. The development of a versatile nickel-catalyzed enantioselective cross-coupling process for electrophiles that bear a leaving group other than a halide adds a significant new dimension to the scope of these reactions.