Diastereoselective Synthesis of Stable Phosphorus Ylides by a Three-Component Reaction between Triphenylphosphine, Dialkyl Acetylenedicarboxylates and 3-(Arylsulfonylhydrazono)Butanoates-Reference-Cited by-同舟云学术

Diastereoselective Synthesis of Stable Phosphorus Ylides by a Three-Component Reaction between Triphenylphosphine, Dialkyl Acetylenedicarboxylates and 3-(Arylsulfonylhydrazono)Butanoates

Published:2013-07 Issue:7 Volume:37 Page:385-387
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Anary-Abbasinejad Mohammad¹,Talebizadeh Mahdiyeh¹,Nikmehr Fereshteh¹

Affiliation:

1. Department of Chemistry, Vali-e-Asr University, Rafsanjan, 77176, Iran

Abstract

Protonation of the reactive 1:1 intermediate produced in the reaction between dialkyl acetylenedicarboxylates and triphenylphosphine by 3-(arylsulfonylhydrazono)butanoates leads to vinylphosphonium salts which undergo Michael addition with the conjugate base of the CH-acid to produce highly functionalised, salt-free phosphorus ylides in a diastereoselective manner and excellent yields.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/174751913X13692122845243

Reference15 articles.

1. Synthesis of Stable Phosphorus Ylides by the Reaction of Ph3P With Activated Acetylenes in the Presence of Dimethyl Methoxymalonate

2. Chemospecific reaction of activated acetylenic compounds with triphenylphosphine in the presence of a system containing two functional groups

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1. Phosphorus Ylides and Related Compounds;Organophosphorus Chemistry;2019-01-04

2. Vinylphosphonium and 2-aminovinylphosphonium salts – preparation and applications in organic synthesis;Beilstein Journal of Organic Chemistry;2017-12-15

3. Chapter 1. Phosphines and related C–P bonded compounds;Organophosphorus Chemistry;2015

4. ChemInform Abstract: Diastereoselective Synthesis of Stable Phosphorus Ylides by a Three-Component Reaction Between Triphenylphosphine, Dialkyl Acetylenedicarboxylates and 3-(Arylsulfonylhydrazono)butanoates.;ChemInform;2013-12-19