Enantioselective Intramolecular Friedel-Crafts-Type α-Arylation of Aldehydes

被引：131
|
作者：
Nicolaou, K. C. [1 ,2 ,3 ]
Reingruber, Ruediger [1 ,2 ,4 ]
Sarlah, David [1 ,2 ]
Braese, Stefan [4 ]
机构：
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[3] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
[4] Univ Karlsruhe TH, Inst Organ Chem, D-76131 Karlsruhe, Germany
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 06期
基金：
美国国家科学基金会;
关键词：
ASYMMETRIC ALDOL REACTIONS; ORGANOCATALYSIS; ACTIVATION;
D O I：
10.1021/ja809405c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Enantioselective organo-SOMO catalysis has, in the last two years, been the subject of considerable development and exploration. A number of new and unique transformations have been reported, such as alpha-allylation, alpha-oxyamination, alpha-enolation, and alpha-vinylation of aldehydes. Herein, we report a modification of this activation mode that involves the intramolecular Friedel-Crafts-type alpha-arylation of aldehydes carrying etectron-donating groups on their aromatic nucleus and its application to the total synthesis of demethyl calamenene, a potent cytotoxic agent against human adenocarcinoma A 549.
引用
收藏
页码：2086 / +
页数：3
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