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A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal.

ABSTRACT: We describe an unusual net [2+2] cycloaddition reaction between boron alkylidenes and unactivated alkenes. This reaction provides a new method for the construction of carbocyclic ring systems bearing versatile organoboronic esters. Aside from surveying the scope of this reaction, we provide details about the mechanistic underpinnings of this process, and examine its application to the synthesis of the natural product aphanamal.

SUBMITTER: Liu X

PROVIDER: S-EPMC5699471 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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A Boron Alkylidene-Alkene Cycloaddition Reaction: Application to the Synthesis of Aphanamal.

Liu Xun X Deaton T Maxwell TM Haeffner Fredrik F Morken James P JP

Angewandte Chemie (International ed. in English) 20170809 38

We describe an unusual net [2+2] cycloaddition reaction between boron alkylidenes and unactivated alkenes. This reaction provides a new method for the construction of carbocyclic ring systems bearing versatile organoboronic esters. Aside from surveying the scope of this reaction, we provide details about the mechanistic underpinnings of this process, and examine its application to the synthesis of the natural product aphanamal. ...[more]

PMID: 28718214

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