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Alkenenitrile Transmissive Olefination: Synthesis of the Putative Lignan “Morinol I”
Author(s) -
Fleming Fraser F.,
Liu Wang,
Yao Lihua,
Pitta Bhaskar,
Purzycki Matthew,
Ravikumar P. C.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101235
Subject(s) - chemistry , lignan , aldehyde , reagent , acrylonitrile , organic chemistry , grignard reagent , stereochemistry , combinatorial chemistry , catalysis , copolymer , polymer
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 forstereoselectively synthesizing alkenes, as illustrated in the synthesis of the putative lignan morinol I.