Titanium-Catalyzed Stereoselective Synthesis of Spirooxindole Oxazolines
Titanium-Catalyzed Stereoselective Synthesis of Spirooxindole Oxazolines
复制标题
DOI：
10.1021/ol1027305
复制
发表时间：
2011-02-04
期刊：
影响因子：
5.2
通讯作者：
Franz, Annaliese K.
中科院分区：
文献类型：
--
作者：
Badillo, Joseph J.;Arevalo, Gary E.;Franz, Annaliese K.
使用催化氯化钛(IV)（10 或 20 mol%）开发了靛红和 5-甲氧基恶唑之间的区域和立体选择性环化，以优异的产率（高达 99%）和非对映选择性（dr > 99:1）提供螺[3,3'-氧吲哚恶唑啉]。恶唑 4 位的取代可控制亲核攻击，从而为 2-恶唑啉或 3-恶唑啉螺环提供出色的 (>99:1) 区域控制。
A regio- and stereoselective cyclization between isatins and 5-methoxyoxazoles has been developed using catalytic titanium(IV) chloride (10 or 20 mol %) to afford spiro[3,3'-oxindoleoxazolines] in excellent yield (up to 99%) and diastereoselectivity (dr >99:1). Substitution at the 4-position of the oxazole controls nucleophilic attack to provide either the 2-oxazoline or 3-oxazoline spirocycle with excellent (>99:1) regiocontrol.