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β‐Silylmethylene Malonate as Versatile Reagent in Organic Synthesis

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β-Silylmethylene malonates (β-SMMs) can be considered as a versatile reagent in organic synthesis to introduce a silicon group in strategic positions of organic frameworks which are otherwise difficult to accomplish for further manipulations. This account chronicles beginning from the synthesis of β-SMMs to their use in complexity generation through novel and/ or known reactions. The outcomes of the reactions are highly influenced by the silicon group.


Abstract

A silicon group plays distinctive role in controlling many organic reactions. In this context a β-silylmethylene malonate (β-SMM) can be considered as a versatile reagent in organic synthesis to introduce a silicon group in strategic positions of organic frameworks for further manipulations. In addition to the chemistry exhibited by alkylidene and arylidene malonates, a β-SMM shows unique reaction attributed to the silicon group. The derived products exhibit enormous potential for the rapid generation of useful intermediates/products which are otherwise difficult to accomplish. This account chronicles our systematic approach beginning from the synthesis of β-SMMs from readily available starting materials, and their use in complexity generation through novel and/ or known reactions. Reactions using β-SMMs such as synthesis of 1-substituted vinylsilanes and their Pd-catalyzed cross-coupling, organocatalytic asymmetric addition of methyl ketones, aldehydes, nitroalkanes and pyrazol-5-ones, and asymmetric 1,3-dipolar cycloaddition with azomethine ylides are highly influenced by the silicon group.

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