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

Ryuji Yoneda; Shinya Harusawa; Takushi Kurihara

doi:10.1039/P19880003163

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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

Ryuji Yoneda, Shinya Harusawa and Takushi Kurihara

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.

Download options Please wait...

Article information

DOI: https://doi.org/10.1039/P19880003163
Article type: Paper

Download Citation

J. Chem. Soc., Perkin Trans. 1, 1988, 3163-3168

Permissions

Request permissions

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

R. Yoneda, S. Harusawa and T. Kurihara, J. Chem. Soc., Perkin Trans. 1, 1988, 3163 DOI: 10.1039/P19880003163

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Fetching data from CrossRef.
This may take some time to load.

Journal of the Chemical Society, Perkin Transactions 1

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

Abstract

Article information

Download Citation

Permissions

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

Search articles by author

Spotlight

Advertisements