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47.1.1.4 Alkenation with Metal Carbenes and Related Reactions

DOI: 10.1055/sos-SD-047-00100

Petasis, N. A.Science of Synthesis, (201047161.

General Introduction

The direct conversion of carbonyl compounds into alkenes using methods that involve metal carbenes or gem-dimetallic species (1,1-dimetallics or carbenoids) is a synthetically valuable process, as it generates many types of products, including alkenes having heteroatom substituents that are not readily available by other methods. The reaction conditions for these metal-mediated carbonyl alkenations are distinctly different and complementary to those involving nucleophilic alkenating agents, such as those used in Wittig-type reactions. As a result, it is often possible to perform carbonyl alkenations that are difficult to accomplish by other methods, including alkenations of base-sensitive or heteroatom-substituted carbonyl compounds, and the preparation of base-sensitive or acid-sensitive alkenation products. In many cases, these carbonyl alkenation reactions are also compatible with other processes and can be used for the overall synthesis of a variety of products that are not easily available by other processes. Several general aspects of the chemistry and synthetic applications of carbonyl alkenations with metal carbenes and related reactions have been reviewed.[‌1‌‌9‌]

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References


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