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New Synthetic Methods Utilizing Conjugate Addition of Nucleophiles to 1-Chlorovinyl p-Tolyl Sulfoxide

โœ Scribed by Tsuyoshi Satoh; Shimpei Sugiyama


Book ID
102008796
Publisher
John Wiley and Sons
Year
2007
Weight
11 KB
Volume
38
Category
Article
ISSN
0931-7597

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Conjugate addition of lithium ester enol
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Addition of the lithium ester enolates to 1-chlorovinyl p-tolyl sulfoxides, which were synthesized from chloromethyl p-tolyl sulfoxide and ketones or aldehydes, gave esters having a tertiary or a quaternary carbon at the 3-position, and chlorine and sulfinyl groups at the 4-position in high to quant

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Enantiomerically pure 1-chlorovinyl p-tolyl sulfoxides having two different substituents at the 2-position were synthesized from unsymmetrical ketones and (R)-(-)-chloromethyl p-tolyl sulfoxide in three steps. Treatment of the 1-chlorovinyl p-tolyl sulfoxides with cyanomethyllithium at -78ยฐC to room