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
收藏
页码：2881 / 2886
页数：6
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