1994Phosphorus, sulfur, and silicon and the related elementsRequires access

Stereoselective Addition of Sulfur-Stabilized Carbanions

Jörg‐Stephan Brunck, Jürgen Voß

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Abstract

The reaction of dithioacetal sulfoxides 2 with different electrophiles was investigated. Sulfoxides 2 were easily deprotonated by different bases and reacted with variuos electrophiles. The carbanion of 2 exhibits configurational stability. Asymmetric induction was observed upon the reaction with prochiral electrophiles. Generation of the carbonyl functionality can easily be performed

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The reaction of dithioacetal sulfoxides 2 with different electrophiles was investigated. Sulfoxides 2 were easily deprotonated by different bases and reacted with variuos electrophiles. The carbanion of 2 exhibits configurational stability. Asymmetric induction was observed upon the reaction with prochiral electrophiles. Generation of the carbonyl functionality can easily be performed

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Available abstract

The reaction of dithioacetal sulfoxides 2 with different electrophiles was investigated. Sulfoxides 2 were easily deprotonated by different bases and reacted with variuos electrophiles. The carbanion of 2 exhibits configurational stability. Asymmetric induction was observed upon the reaction with prochiral electrophiles. Generation of the carbonyl functionality can easily be performed

Key concepts: Carbanion, Electrophile, Deprotonation, Sulfur, Stereoselectivity, Chemistry, Electrophilic addition, Asymmetric induction

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