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首页> 外文期刊>Chemistry: A European journal >Rhodium-Catalyzed Spirocyclic Sultam Synthesis by [3+2] Annulation with Cyclic N-Sulfonyl Ketimines and Alkynes
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Rhodium-Catalyzed Spirocyclic Sultam Synthesis by [3+2] Annulation with Cyclic N-Sulfonyl Ketimines and Alkynes

机译：环N-磺酰基酮亚胺和炔烃的[3 + 2]环合反应铑催化的螺环合磺酰胺的合成

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摘要

Functionalized sulfonamides such as sultams and sulfamidates have been used as key intermediates to synthesize diverse biologically active compounds. Strategies for synthesizing sultam derivatives increasingly rely on transition metal-catalyzed bond formation. In fact, catalytic addition of organometallic reagents to sulfonamides offers one of the most reliable methods for constructing sultams with an a-polysubstituted carbon stereocenter. Synthesizing spirocyclic sultams, however, has proven significantly more difficult for organic chemists, and a breakthrough came with the application of metal catalytic [3+2] tandem reaction sequences. Building on the pioneering work of Takai in 2005, the research groups of Cramer, Zhao,and Cheng independently showed that metal alkenyl intermediates generated by alkyne insertion can undergo Grignard-type [3+2] annulation to imine groups (Scheme 1 a). Activating the C-H bond to generate reactive organometallic intermediates is an eco-friendly alternative to conventional catalytic addition methods.
机译：官能化的磺酰胺，如阿马酸和磺酰胺已被用作合成各种生物活性化合物的关键中间体。合成sultam衍生物的策略越来越依赖于过渡金属催化的键形成。实际上，将有机金属试剂催化添加到磺酰胺中是提供一种构建带有a-多取代碳立构中心的sultams的最可靠方法之一。然而，合成螺环合sultams已证明对有机化学家而言更加困难，并且突破了金属催化[3 + 2]串联反应序列的应用。在2005年Takai的开拓性工作的基础上，Cramer，Zhao和Cheng的研究小组独立地表明，由炔烃插入生成的金属烯基中间体可以经过格氏（Grignard）型[3 + 2]环化成亚胺基（方案1 a）。活化C-H键以生成反应性有机金属中间体是传统催化加成方法的环保替代品。

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