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Alkenenitrile Transmissive Olefination: Synthesis of the Putative Lignan "Morinol I"

ABSTRACT: Grignard reagents trigger an addition-elimination with ?'-hydroxy acrylonitriles to selectively generate Z-alkenenitriles. The modular assembly of Z-alkenenitriles from a Grignard reagent, acrylonitrile, and an aldehyde is ideal for stereoselectively synthesizing alkenes as illustrated in the synthesis of the putative lignan "morinol I."

SUBMITTER: Fleming FF

PROVIDER: S-EPMC3336159 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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Alkenenitrile Transmissive Olefination: Synthesis of the Putative Lignan "Morinol I"

Fleming Fraser F FF Liu Wang W Yao Lihua L Pitta Bhaskar B Purzycki Matthew M Ravikumar P C PC

European journal of organic chemistry 20111028 34

Grignard reagents trigger an addition-elimination with α'-hydroxy acrylonitriles to selectively generate Z-alkenenitriles. The modular assembly of Z-alkenenitriles from a Grignard reagent, acrylonitrile, and an aldehyde is ideal for stereoselectively synthesizing alkenes as illustrated in the synthesis of the putative lignan "morinol I." ...[more]

PMID: 22545004

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