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Sulfoxides, vinyl addition reaction with enolates

Treatment of chiral, nonracemic vinyl sulfoxides (214) with O-silylated ketene acetal (215) in the presence of a catalytic amount of zinc chloride resulted in an enantioselective additive Pummerer-type reaction, affording the corresponding enantiomerically enriched methyl-4-siloxy-4-sulfenylbuyrate (216) (Scheme 55).122 This is the overall addition of the enolate equivalent to the vinyl sulfoxide. [Pg.197]

An intramolecular version of enolate Michael addition to enantiomerically pure vinylic sulfoxides is represented by reaction of a cyclopentenone sulfoxide with dichloroketene (Scheme 5)90 this type of additive Pummerer rearrangement has been developed by Marino and coworkers91 into a highly effective way of constructing variously substituted lactones in very high enantiomeric purity (equation 43). [Pg.843]


See other pages where Sulfoxides, vinyl addition reaction with enolates is mentioned: [Pg.194]    [Pg.325]    [Pg.234]    [Pg.71]    [Pg.31]    [Pg.151]    [Pg.1922]    [Pg.170]   
See also in sourсe #XX -- [ Pg.100 , Pg.102 ]

See also in sourсe #XX -- [ Pg.4 , Pg.100 , Pg.102 ]

See also in sourсe #XX -- [ Pg.4 , Pg.100 , Pg.102 ]




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Enolate Additions

Enolate vinylation

Enolates addition reactions

Enols addition reactions

Enols reactions with

Reaction with sulfoxides

Reactions, with enolates

Sulfoxidation reactions

Sulfoxides additions

Sulfoxides, vinyl

Vinyl addition

Vinyl reaction

Vinyl sulfoxide

Vinyl sulfoxides sulfoxide

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