Synthesis of (Z)-predominant α,β-unsaturated nitriles from enone cyanohydrin diethyl phosphates: application to the synthesis of (±)-nuciferal, (±)-(E)- and -(Z)-nuciferol, and (±)-manicone
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 3163-3168
- https://doi.org/10.1039/p19880003163
Abstract
Enone cyanohydrin diethyl phosphates reacted regio- and stereo-selectively with a variety of organocopper reagents to give γ-coupling products, (Z)-predominant alk-2-enenitriles. The methodology was applied to the synthesis of (±)-nuciferal, (±)-(E)- and -(Z)-nuciferol, and (±)-manicone.This publication has 2 references indexed in Scilit:
- Transition-metal-catalysed Grignard reaction of secondary allylic phosphatesJournal of the Chemical Society, Perkin Transactions 1, 1984
- Pheromone synthesis. 3. A synthesis of (E)-4,6-dimethyl-4-octen-3-one (manicone)The Journal of Organic Chemistry, 1976