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Original Articles

(Diphenoxyphosphoryl)methyl p-tolyl sulfoxide: A new reagent for Z-selective synthesis of racemic and optically active vinyl sulfoxides

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Pages 535-540 | Received 03 Sep 2015, Accepted 06 Oct 2015, Published online: 17 Mar 2016
 

GRAPHICAL ABSTRACT

ABSTRACT

Racemic and optically active (+)-(S)-(diphenoxyphosphoryl)methyl p-tolyl sulfoxide were prepared and used as Horner olefination reagents. Their reaction with aromatic and aliphatic aldehydes afforded the corresponding racemic and enantiomeric α,β-unsaturated sulfoxides with moderate to high Z-selectivity. The E/Z ratio was found to be dependent on the structure of aldehyde, nature of base, reaction conditions, and addition of 18-crown-6.

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