Conjugate Additions to Alkylidene Bis(Sulfoxides)

被引：6

作者：

Brebion, Franck ^{[1
]}

Vincent, Guillaume ^{[1
]}

Chelli, Saloua ^{[1
]}

Kwasnieski, Ophelie ^{[1
]}

Najera, Francisco ^{[1
]}

Delouvri, Benedicte ^{[1
]}

Marek, Ilan ^{[2
,3
]}

Derat, Etienne ^{[1
]}

Goddard, Jean-Philippe ^{[1
]}

Malacria, Max ^{[1
]}

Fensterbank, Louis ^{[1
]}

机构：

[1] Univ Paris 06, UPMC, Inst Parisien Chim Mol, UMR CNRS 7201, F-75005 Paris, France

[2] Technion Israel Inst Technol, Mallat Family Lab Organ Chem, Schulich Fac Chem, IL-32000 Haifa, Israel

[3] Technion Israel Inst Technol, Lise Meitner MinerVa Ctr Computat Quantum Chem, IL-32000 Haifa, Israel

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2011年 / 6卷 / 07期

关键词：

azides; bis(sulfoxides); diastereoselectivity; ketene equivalent; Michael addition; DIELS-ALDER REACTIONS; CHIRAL KETENE EQUIVALENT; DIASTEREOSELECTIVE MICHAEL ADDITIONS; ASYMMETRIC-SYNTHESIS; BIS-SULFOXIDES; DOMINO REACTIONS; ALPHA; BETA-UNSATURATED SULFOXIDES; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CYCLOADDITION REACTIONS;

D O I：

10.1002/asia.201000904

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general study on the conjugate addition of anionic nucleophiles to alkylidene bis(sulfoxides) is presented. Alkoxides gave high yielding and diastereoselective addition reactions, which could be influenced by solvents and the counteranion. Azides provided an interesting entry into sulfinyl-substituted triazoles. Organometallics, mainly copper reagents, proved also to be valuable nucleophiles, and complete inversion of the stereoselectivity was achieved in the addition reaction with the latter. Modelizations provide a rationale for the observed diastereoselectivity.

引用

页码：1825 / 1833

页数：9

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