Alkylidene[1,3]dithiolane-1,3-dioxides as Potent Michael-Type Acceptors

Abstract

Nucleophilic additions of enolates, piperidine and methanol to easily prepared alkylidene[1,3]dithiolane-1,3-dioxides afforded the respective adducts with good yields. Selectivities were strongly dependant from the steric hindrance of the substrate and reached 92:8 to ÷98:2 in additions to the phenyl-substituted bissulf­oxide product.

Key words

nucleophilic additions - sulfoxides - thioacetals - Umpolung - stereoelectronic effects

References and Notes

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12

The formation of methanol adducts and of the prop-1-enyl derivative was avoided when CH₂Cl₂-acetone (2:1) was used as eluent in the chromatography.

13

CCDC 603241 (co-crystal of 3c and 7c) and CCDC 603242 (5c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

15

Klopper, W.; Bihlmeier, A.; Kordel, E. personal communication.