1396318-59-4

Basic information

• Product Name: (1'R,2'S,3R,7a'R)-1-methyl-5-bromo-2-oxo-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizine]-2'-carboxylic acid
• Synonyms: (1'R,2'S,3R,7a'R)-1-methyl-5-bromo-2-oxo-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizine]-2'-carboxylic acid
• CAS NO: 1396318-59-4
• Molecular Weight: 441.324
• Mol File: 1396318-59-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1'R,2'S,3R,7a'R)-1-methyl-5-bromo-2-oxo-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizine]-2'-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1'R,2'S,3R,7a'R)-1-methyl-5-bromo-2-oxo-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizine]-2'-carboxylic acid(1396318-59-4)
• EPA Substance Registry System: (1'R,2'S,3R,7a'R)-1-methyl-5-bromo-2-oxo-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizine]-2'-carboxylic acid(1396318-59-4)

Safety Data

• Hazardous Substances Data: 1396318-59-4(Hazardous Substances Data)

Upstream product

• 1571075-61-0 3-((3R,6'S,7'R,7a'R)-5-bromo-1-methyl-2-oxo-7'-phenyl-1',2',3',6',7',7a'-hexahydrospiro[indoline-3,5'-pyrrolizin]-6'-ylcarbonyl)oxazolidin-2-one 
• 2058-72-2 5-bromo-1-methyl-1H-indole-2,3-dione 
• 141209-95-2 (4S)-4-phenyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 
• 1396318-50-5 (S)-3-((1'R,2'S,3R,7a'R)-5-bromo-1-methyl-2-oxo-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizin]-2'-ylcarbonyl)-4-phenyloxazolidin-2-one 

Relevant articles and documents

An efficient, one-pot, three-component procedure for the synthesis of chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition

The catalytic, highly regio-, diastereo-, and enantioselective synthesis of a small library of chiral spirooxindolopyrrolizidines via a three-component 1,3-dipolar cycloaddition reaction of azomethine ylides, derived from isatin, with electron-deficient dipolarophiles, 3-(2-alkenoyl)-1,3-oxazolidin-2-ones, is described. A chiral copper(II) complex of cyclohexane-1,2- bis(arylmethyleneamine) catalyzed this process at room temperature. The reaction mechanism is discussed on the basis of the assignment of the absolute configuration of the cycloadducts.

Synthesis of new enantiomerically pure spirooxindolopyrrolizidines via a three-component asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides derived from isatin

An efficient, one-pot, three-component procedure for the synthesis of a small library of new chiral spirooxindolopyrrolizidines with high regio-, diastereo-, and enantioselectivity, from the 1,3-dipolar cycloaddition of azomethine ylides and optically active cinnamoyl oxazolidinone is described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the absence of any Lewis acids. The oxazolidinone chiral auxiliary is removed in a non-destructive manner. The reaction mechanism is discussed on the basis of the assignment of the absolute configuration of the cycloadducts, and on theoretical calculations.