Enantioselective Synthesis of Pyrroloindolines by a Formal [3+2] Cycloaddition Reaction

被引：175
|
作者：
Repka, Lindsay M. [1 ]
Ni, Jane [1 ]
Reisman, Sarah E. [1 ]
机构：
[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 41期
关键词：
STREPTOMYCES SP SUC1; BRONSTED ACID; CHIRAL DIOLS; ASYMMETRIC ALLYLBORATION; LEWIS-ACID; ALKALOIDS; CONSTRUCTION; STRATEGY; EXAMPLE; ENONES;
D O I：
10.1021/ja107328g
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(R)-BINOL center dot SnCl4 was found to catalyze a formal [3 + 2] cycloaddition reaction between C(3)-substituted indoles and 2-amidoacrylates to provide pyrroloindolines. A variety of pyrroloindolines were prepared with high enantioselectivity in one step from simple precursors. This methodology is expected to facilitate the total synthesis of pyrroloindoline alkaloids, an important class of biologically active natural products.
引用
收藏
页码：14418 / 14420
页数：3
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