215439-15-9

Basic information

• Product Name: (S_S,2S,3R) methyl 3--3-phenyl-2-vinylpropanoate
• Synonyms: (S_S,2S,3R) methyl 3--3-phenyl-2-vinylpropanoate
• CAS NO: 215439-15-9
• Molecular Weight: 343.447
• Mol File: 215439-15-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S_S,2S,3R) methyl 3--3-phenyl-2-vinylpropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S_S,2S,3R) methyl 3--3-phenyl-2-vinylpropanoate(215439-15-9)
• EPA Substance Registry System: (S_S,2S,3R) methyl 3--3-phenyl-2-vinylpropanoate(215439-15-9)

Safety Data

• Hazardous Substances Data: 215439-15-9(Hazardous Substances Data)

Upstream product

• 3724-55-8 methyl but-3-enoate 
• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 

Relevant articles and documents

Enantiomerically pure α-alkylidene β-amino esters from asymmetric addition of metal dienolates to N-sulfinylimines

Lithium dienolate of 3-butenoic methyl ester was reacted with enantiomerically pure N-arylsulfinyl phenylimines (1 and 2) under different conditions. The reactions were completely regioselective -the C-C coupling occurs at the 2-position of dienolate - and highly stereoselective at the iminic carbon. In the presence of different Lewis acids (ZnCl2, ZnBr2, and ScTf3) mixtures of two α-vinyl, β-arylsulfmylamino esters (epimers at C-α) were obtained, being the stereoselectivity depending on the nature of the aryl sulfinyl moiety and the Lewis acid used. Desulfinylation of these mixtures followed by isomerization of the double bond with Na2CO3 allowed the synthesis of the optically pure CE)-α-ethylidene-β-amino ester 10 in quite high overall yield. The addition of the lithium dienolate to sulfinylimines in the absence of the Lewis catalysts yielded mixtures containing important amounts of the optically pure N-arylsulfinyl α-ethylidene-β-amino esters, which became the exclusive product of the reaction when N-2-methoxynaphthylsulfinyl phenylimine 2 was used as starting product.