Strategies for the enantioselective synthesis of spirooxindoles
Strategies for the enantioselective synthesis of spirooxindoles
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DOI：
10.1039/c2ob25184a
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发表时间：
2012-01-01
影响因子：
3.2
通讯作者：
Franz, Annaliese K.
中科院分区：
文献类型：
--
作者：
Ball-Jones, Nicolas R.;Badillo, Joseph J.;Franz, Annaliese K.
羟吲哚和螺羟吲哚是重要的合成靶标，其通常被认为在其生物活性和用于药物先导发现的应用方面是预先验证的。本文综述了2010年和2011年报道的螺环羟吲哚的对映选择性合成策略。虽然对映选择性合成仍然是一个持续的挑战，令人兴奋的最近进展，在这一领域的功能螺羟吲哚更复杂，多达8个立体中心，更实用的合成方法，和新的催化活化策略。催化剂体系和反应条件的发展表明，许多反应可以优化，以控制选择性，并提供异构体的产品，这是重要的生物测试。这篇综述是基于两种主要的断开策略组织的，然后进一步细分为所产生的螺环的类型和环大小。还比较了非螺环3，3 '-二取代羟吲哚的合成策略。
Oxindoles and spirooxindoles are important synthetic targets that are often considered to be prevalidated with respect to their biological activity and applications for pharmaceutical lead discovery. This review features efficient strategies for the enantioselective synthesis of spirocyclic oxindoles, focusing on reports in 2010 and 2011. Although enantioselective synthesis remains an ongoing challenge, exciting recent advances in this area feature spirooxindoles with greater complexity, up to eight stereogenic centers, more practical synthetic methods, and new catalytic activation strategies. Developments in catalyst systems and reaction conditions have shown that many reactions can be optimized to control selectivity and provide access to isomeric products, which are important for biological testing. This review is organized based on two primary disconnection strategies, and then further subdivided into the type and ring size of the spirocycle that is generated. Strategies are also compared for the synthesis of non-spirocyclic 3,3'-disubstituted oxindoles.