钪(III)催化的异吲哚啉酮的对映选择性烯丙基化反应使用烯丙基硅烷。

Scandium(III)-catalyzed enantioselective allylation of isatins using allylsilanes.

机构信息

Department of Chemistry, University of California, One Shields Avenue, Davis, California 95616, United States.

出版信息

Org Lett. 2012 May 4;14(9):2218-21. doi: 10.1021/ol300496v. Epub 2012 Apr 16.

Abstract

The scandium(III)-catalyzed enantioselective Hosomi-Sakurai allylation of isatins with various substituted allylic silanes is described. A catalyst loading as low as 0.05 mol % is utilized at room temperature to afford the 3-allyl-3-hydroxy-2-oxindoles in excellent yields and enantioselectivity up to 99% ee, including a demonstration of a gram-scale reaction. The effects of additives and varying silyl groups were explored to demonstrate the scope and application.

摘要

本文描述了钪(III)催化的各种取代烯丙基硅烷对异色满的对映选择性霍斯米-萨库赖烯丙基化反应。在室温下，只需使用低至 0.05 mol%的催化剂负载量，即可以优异的收率和高达 99%ee 的对映选择性得到 3-烯丙基-3-羟基-2-氧吲哚，包括一个克级规模反应的演示。还研究了添加剂和不同硅基的影响，以展示其适用范围。