One-Pot Hydroxy Group Activation/Carbon-Carbon Bond Forming Sequence Using a Bronsted Base/Bronsted Acid System

被引：40

作者：

Devineau, Alice ^{[1
]}

Pousse, Guillaume ^{[2
]}

Taillier, Catherine ^{[1
]}

Blanchet, Jerome ^{[2
]}

Rouden, Jacques ^{[2
]}

Dalla, Vincent ^{[1
]}

机构：

[1] Univ Havre, URCOM, EA 3221, FR3038, F-76058 Le Havre, France

[2] Univ Caen Basse Normandie, ENSICAEN, Lab Chim Mol & Thioorgan, UMR 6507,CNRS,INC3M,FR3038, F-14050 Caen, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 17期

关键词：

N-acyliminium; alkylation; electrophilic alcohols; sequential organocatalysis; trichloroacetimidates; NUCLEOPHILIC-SUBSTITUTION REACTIONS; ACYLIMINIUM ION CHEMISTRY; SITE-ISOLATED BASE; ALPHA-AMIDOALKYLATION; HIGHLY EFFICIENT; CATALYSTS; ALCOHOLS; TRIFLATE; ACETATES;

D O I：

10.1002/adsc.201000602

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new sequential two-step multicatalytic strategy is presented consisting in the efficient DBU-catalysed trichloroacetimidation of an alcohol followed by a ditriflylamine (Tf2NH)-catalysed intermolecular alkylation by silicon-based nucleophiles and C-H nucleophiles. The distinct feature of the trichloroacetimidate group allows use of weaker acid catalysts such as 1,1'-bi-2-naphthol (BINOL)-derived phosphoric acid, pointing out the possible development of an enantioselective variant. This unprecedented sequential one-pot Bronsted base-Bronsted acid catalysis further expands the synthetic scope of the trichloroacetimidate group.

引用

页码：2881 / 2886

页数：6

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