Issue 3, 2002
From the journal:

Chemical Communications

Diels–Alder chemistry of 2-diethoxyphosphinylcyclohex-2-enones. A new approach to complex phosphonates and synthetic applications of the β-keto phosphonate system

Chiung-Fang Chien,a   Jen-Dar Wu,a   Tai Wei Ly,b   Kak-Shan Shiac  and  Hsing-Jang Liu*ab  

* Corresponding authors

a Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan, Republic of China
E-mail: hjliu@mx.nthu.edu.tw;
Fax: + 886-3-5734292

b Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan, Republic of China

c Division of Biotechnology and Pharmaceutical Research, National Health Research Institutes, Nankang, Taipei, Taiwan, Republic of China

Abstract

Enone phosphonates 1 and 2 were found to be excellent dienophiles for the Diels–Alder reaction, giving phosphonate-containing polycycles, and the phosphonate group of the resulting adducts facilitated both the installation of an angular alkyl group via a reductive alkylation process and the regioselective generation of a ring junction double bond via an intramolecular Wadsworth–Horner–Emmons reaction.

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Article information

DOI
https://doi.org/10.1039/B109780F
Article type
Communication
Submitted
25 Oct 2001
Accepted
23 Nov 2001
First published
17 Jan 2002

Chem. Commun., 2002, 248-249

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Diels–Alder chemistry of 2-diethoxyphosphinylcyclohex-2-enones. A new approach to complex phosphonates and synthetic applications of the β-keto phosphonate system

C. Chien, J. Wu, T. W. Ly, K. Shia and H. Liu, Chem. Commun., 2002, 248 DOI: 10.1039/B109780F

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