Palladium-Catalyzed (3+2) and (4+2) Cycloaddition Reactions of Sulfamidate Imine-Derived Azadienes: Synthesis of Spirocyclic Pyrrolidines and Tetrahydroquinolines,The Journal of Organic Chemistry

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Palladium-Catalyzed (3+2) and (4+2) Cycloaddition Reactions of Sulfamidate Imine-Derived Azadienes: Synthesis of Spirocyclic Pyrrolidines and Tetrahydroquinolines
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-08-29 , DOI: 10.1021/acs.joc.4c01425
Chi Bong Eric Chao ₁ , Quoc Hoang Pham ₁ , Christopher Richardson ₁ , Stephen G Pyne ₁ , Christopher J T Hyland ₁

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Diastereoselective Pd-catalyzed (3+2) and (4+2) cycloaddition reactions of sulfamidate imine-derived 1-azadienes with zwitterionic N-dipoles derived from 1-tosyl-2-vinylaziridine and 4-vinylbenzoxazinone have been developed. These reactions provide highly functionalized azaspirocycles featuring three contiguous stereocenters. The sulfonyl imine moiety of the cycloadducts can be fully reduced to access valuable β-amino alcohols.

中文翻译：

钯催化磺胺亚胺衍生的氮杂二烯的 (3+2) 和 (4+2) 环加成反应：螺环吡咯烷和四氢喹啉的合成

已经开发出磺酰胺亚胺衍生的 1-氮杂二烯与衍生自 1-甲苯磺酰基-2-乙烯基氮丙啶和 4-乙烯基苯并恶嗪酮的两性离子 N-偶极子的非对映选择性 Pd 催化 (3+2) 和 (4+2) 环加成反应。这些反应提供了具有三个连续立体中心的高度功能化的氮杂螺环。环加合物的磺酰亚胺部分可以被充分还原，得到有价值的β-氨基醇。

更新日期：2024-08-29

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