1609976-43-3

Basic information

• Product Name: (1'S,3R)-diethyl-1-benzyl-1'-(4-chlorophenyl)-2-oxo-1',2'-dihydrospiro[indoline-3,4'-pyrido[3,4-b]indole]-3',3'(9'H)-dicarboxylate
• CAS NO: 1609976-43-3
• Molecular Weight: 634.131
• Mol File: 1609976-43-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1'S,3R)-diethyl-1-benzyl-1'-(4-chlorophenyl)-2-oxo-1',2'-dihydrospiro[indoline-3,4'-pyrido[3,4-b]indole]-3',3'(9'H)-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1'S,3R)-diethyl-1-benzyl-1'-(4-chlorophenyl)-2-oxo-1',2'-dihydrospiro[indoline-3,4'-pyrido[3,4-b]indole]-3',3'(9'H)-dicarboxylate(1609976-43-3)
• EPA Substance Registry System: (1'S,3R)-diethyl-1-benzyl-1'-(4-chlorophenyl)-2-oxo-1',2'-dihydrospiro[indoline-3,4'-pyrido[3,4-b]indole]-3',3'(9'H)-dicarboxylate(1609976-43-3)

Safety Data

• Hazardous Substances Data: 1609976-43-3(Hazardous Substances Data)

Upstream product

• 6829-40-9 aminomalonic acid diethyl ester 
• 676612-41-2 1′-benzyl-3′-hydroxy-1′,3′-dihydro-1H,2′H-3,3′-biindol-2′-one 
• 104-88-1 4-chlorobenzaldehyde 

Relevant articles and documents

Catalytic asymmetric formal [3+3] cycloaddition of an azomethine ylide with 3-indolylmethanol: Enantioselective construction of a six-membered piperidine framework

A catalytic asymmetric formal [3+3] cycloaddition of 3-indolylmethanol and an in situ-generated azomethine ylide has been established to construct a chiral six-membered piperidine framework with two stereogenic centers. This approach not only represents the first enantioselective cycloaddition of isatin-derived 3-indolylmethanol, but also has realized an unusual enantioselective formal [3+3] cycloaddition of azomethine ylide rather than its common [3+2] cycloadditions. Besides, this protocol combines the merits of a multicomponent reaction and organocatalysis, which efficiently assembles a variety of isatin-derived 3-indolylmethanols, aldehydes, and amino esters into structurally diverse spiro[indoline-3,4′-pyridoindoles] with one all-carbon quaternary stereogenic center in high yields and excellent enantioselectivities (up to 93 % yield, >99 % enantiomeric excess (ee)). Although the diastereoselectivity of the reaction is generally moderate, most of the diastereomers can be separated by using column chromatography followed by preparative TLC. An unusual addition: The first catalytic asymmetric formal [3+3] cycloaddition of isatin-derived 3-indolylmethanol with an in situ-generated azomethine ylide has been established to construct a chiral six-membered piperidine framework with two stereogenic centers. This approach represents the first enantioselective cycloaddition of isatin-derived 3-indolylmethanol, and it has realized an unusual enantioselective formal [3+3] cycloaddition of the azomethine ylide (DCEa =a 1,2-dichloroethane). Copyright