Publication

Highly cis-selective Wittig reactions employing a-heterosubstituted ylides

Manfred Schlosser
1993
Journal Articles

Abstract

1-Alkenyl chlorides, bromides or iodides, e.g., cis-1-chloro-1-octene, can be obtained with very high cis selectivities by Wittig reactions with a-chloro, a-bromo and a-iodo ylides derived from (2-MeOCH2C6H4)3P. The corresponding a-methoxy substituted ylide produces enol ethers with remarkably high cis/trans ratios. Pd(II)-catalyzed coupling of (Z)-1-iodo-1-heptene with Et acrylate affords Et (2E,4Z)-2,4-decadienoate, the Bartlett pear fragrance, in almost quant. yield. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/e8b004af-b255-46b8-9ea4-59cd8be7af3a

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Manfred Schlosser
1993
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/e8b004af-b255-46b8-9ea4-59cd8be7af3a

About this result

Related concepts (8)

Coupling reaction

In organic chemistry, a coupling reaction is a type of reaction in which two reactant molecules are bonded together. Such reactions often require the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M (where R = organic group, M = main group centre metal atom) reacts with an organic halide of the type R'-X with formation of a new carbon-carbon bond in the product R-R'. The most common type of coupling reaction is the cross coupling reaction. Richard F.

Cross-coupling reaction

In organic chemistry, a cross-coupling reaction is a reaction where two different fragments are joined. Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal catalysts. One important reaction type is this: (R, R' = organic fragments, usually aryle; M = main group center such as Li or MgX; X = halide) These reactions are used to form carbon–carbon bonds but also carbon-heteroatom bonds. Cross-coupling reaction are a subset of coupling reactions.

Kumada coupling

In organic chemistry, the Kumada coupling is a type of cross coupling reaction, useful for generating carbon–carbon bonds by the reaction of a Grignard reagent and an organic halide. The procedure uses transition metal catalysts, typically nickel or palladium, to couple a combination of two alkyl, aryl or vinyl groups. The groups of Robert Corriu and Makoto Kumada reported the reaction independently in 1972. The reaction is notable for being among the first reported catalytic cross-coupling methods.