218439-10-2

Basic information

• Product Name: 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane
• Synonyms: 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane
• CAS NO: 218439-10-2
• Molecular Weight: 479.515
• Mol File: 218439-10-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane(218439-10-2)
• EPA Substance Registry System: 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane(218439-10-2)

Safety Data

• Hazardous Substances Data: 218439-10-2(Hazardous Substances Data)

Upstream product

• 603-35-0 triphenylphosphine 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 104324-16-5 (4S)-(+)-3-(chloroacetyl)-4-(phenylmethyl)-2-oxazolidinone 
• 129549-13-9 4S-3-(2-bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone 
• 139278-12-9 (4S)-4-benzyl-3-<2-(triphenylphosphonio)acetyl>-2-oxazolidinone bromide 

Downstream Products

• 174003-89-5 (4S)-3-<(E)-4'bromo-4',4'-difluoro-2'-butanoyl>-4-benzyl-2-oxazolidinone 
• 218439-14-6 (S)-4-Benzyl-3-[(E)-(S)-4-(tert-butyl-dimethyl-silanyloxy)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoyl]-oxazolidin-2-one 
• 505093-89-0 (4S)-3-[cis-(4-t-butoxycarbonylaminocyclohexyl)propenoyl]-4-phenylmethyl-2-oxazolidinone 
• 505093-89-0 (4S)-3-[trans-(4-t-butoxycarbonylaminocyclohexyl)propenoyl]-4-phenylmethyl-2-oxazolidinone 
• 174003-91-9 (2R,1'R,2'R,4S)-ethyl N-diphenylmethylidene-2-<2'-<(4-benzyl-2-oxazolidinon-3-yl)carbonyl>-3',3'-difluoro>cyclopropylglycinate 
• 218439-16-8 (S)-4-Benzyl-3-[(2S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butyryl]-oxazolidin-2-one 
• 218439-38-4 (S)-4-Benzyl-3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyryl]-oxazolidin-2-one 
• 922174-49-0 (4S,2'S,6'S)-3-(2',6'-dimethyl-7'-carboxyheptanoyl)-4-phenylmethyl-1,3-oxazolidin-2-one 
• 922174-48-9 (4S,2'S,6'R)-3-(2',6'-dimethyl-7'-carboxyheptanoyl)-4-phenylmethyl-1,3-oxazolidin-2-one 
• 922174-45-6 (4S,2'S,6'S)-3-[2',6'-dimethyl-8'-(tetrahydro-2H-pyran-2-yloxy)octanoyl]-4-phenylmethyl-1,3-oxazolidin-2-one 
• 922174-44-5 (4S,2'S,6'R)-3-[2',6'-dimethyl-8'-(tetrahydro-2H-pyran-2-yloxy)octanoyl]-4-phenylmethyl-1,3-oxazolidin-2-one 
• 922174-42-3 (4S,6'S)-3-[6'-methyl-8'-(tetrahydro-2H-pyran-2-yloxy)octanoyl]-4-phenylmethyl-1,3-oxazolidin-2-one 

Relevant articles and documents

Stereoselective Visible-Light Catalyzed Cyclization of Bis(enones): A Viable Approach to the Synthesis of Enantiomerically Enriched Cyclopentane Rings

Photoredox catalytic cyclization of aryl enones in the presence of visible light, promoted either by metals or organic dyes, represent a valuable strategy for the synthesis of cycloalkanes. The development of a stereoselective version of such transformation, in the presence of the metal-free catalyst Eosin Y was studied, with the aim to realize an efficient protocol for the in-flow synthesis of enantiomerically enriched functionalized cyclopentane rings, taking advantage of the flow reactors technology. The use of a chiral auxiliary on the bisenone to be cyclized offers a straightforward and convenient option to exert a stereocontrol on the light-driven cyclization. By exploiting Evans’ oxazolidinones, the stereoselective light-driven cyclization affords, after the removal of the chiral auxiliary, a functionalized 1,2-trans cyclopentane ring in up to 83/17 enantiomeric ratio. When the reaction was performed in continuo, in a homemade coil photoreactor, high yields were observed. The cyclization was also successfully realized in a 3D-printed mesoreactor, without any change in the diastereoseletctivity of the process.

A highly diastereoselective synthesis of trans-3,4-(difluoromethano)glutamic acid

Reaction of enantiomerically pure N-(4'-bromo-4',4'-difluorocrotonoyl)oxazolidinone 5 with lithium enolate of N-diphenylmethylideneglycinate 6 in DMF proceeded in highly diastereoselective manner to give trans-disubstituted gem-difluorocyclopropane 7, which was readily converted to the 3,4-(difluoromethano)glutamic acid 4.