Formation of Functionalized Carbocycles via Base-Promoted Ring Opening/Brook Rearrangement/Allylic Alkylation of gamma-Silyl-beta,gamma-epoxybutanenitrile Followed by Nitrile Anion Cyclization with Bis-Electrophiles

Tatsuya Matsumoto; Hyuma Masu; Kentaro Yamaguchi

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Formation of Functionalized Carbocycles via Base-Promoted Ring Opening/Brook Rearrangement/Allylic Alkylation of gamma-Silyl-beta,gamma-epoxybutanenitrile Followed by Nitrile Anion Cyclization with Bis-Electrophiles

机译：经由碱促进的γ-甲硅烷基-β，γ-环氧丁腈腈基开环/布鲁克重排/烯丙基烷基化反应，然后与双亲电子的腈阴离子环化反应，形成功能化的摩托车

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Reaction of gamma-silyl-beta,gamma-epoxybutanenitrile with a base generates an a-nitrile carbanion derivative of 4-siloxybut-3-enenitrile,which undergoes reaction with bis-electrophiles such as 1,omega-dihaloalkanes,omega-bromo-alpha-beta-unsaturated esters,and bisenoates to provide highly functionalized carbocycles.

机译：γ-甲硅烷基-β，γ-环氧丁腈与碱反应生成4-甲氧基丁-3-烯腈的α-碳负离子衍生物，该衍生物与双亲电子试剂反应，例如1，ω-二卤代烷烃，ω-溴代α-烯烃-β-不饱和酯和双烯酸酯，可提供高度官能化的碳环。

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《Organic letters》 |2004年第23期|共4页
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Tatsuya Matsumoto; Hyuma Masu; Kentaro Yamaguchi;
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1. Formation of Functionalized Carbocycles via Base-Promoted Ring Opening/Brook Rearrangement/Allylic Alkylation of gamma-Silyl-beta,gamma-epoxybutanenitrile Followed by Nitrile Anion Cyclization with Bis-Electrophiles [J] . Tatsuya Matsumoto, Hyuma Masu, Kentaro Yamaguchi Organic letters . 2004,第23期

机译：经由碱促进的γ-甲硅烷基-β，γ-环氧丁腈腈基开环/布鲁克重排/烯丙基烷基化反应，然后与双亲电子的腈阴离子环化反应，形成功能化的摩托车
2. Tandem Base-Promoted Ring Opening/Brook Rearrangement/Allylic Alkylation of O-Silyl Cyanohydrins of β-Silyl-α,β-epoxyaldehydes [J] . Kei Takeda, Eiji Kawanishi, Michiko Sasaki, Organic letters . 2002,第9期

机译：β-甲硅烷基-α，β-环氧醛的O-甲硅烷基氰醇的串联碱基促进的开环/布鲁克重排/烯丙基烷基化
3. Synthesis of 7-Membered Ring Carbocycles via a Palladium- Catalyzed Intramolecular Allylic Alkylation-Isomerization-Cope Rearrangement Cascade [J] . Kazuki Tsuruda, Takahisa Tokumoto, Naoya Inoue, European journal of organic chemistry . 2018,第22期

机译：通过钯 - 催化的分子内烯丙基烷基化 - 应对重排级联合成7-元环碳缩醛克服
4. I. Studies on the organocatalytic formation of quaternary stereocenters. ii. Studies on the claisen rearrangement as a route to quaternary stereocenters. iii. Asymmetric synthesis of aldehydes bearing quaternary carbon centers via the decarboxylative asymmetric allylic alkylation. [D] . Alberch, Eduardo. 2013

机译：I.季铵立体中心的有机催化形成研究。 ii。关于克莱森重排作为四元立体中心路径的研究。 iii。通过脱羧不对称烯丙基烷基化反应不对称合成带有季碳中心的醛。
5. Anion Relay Chemistry: Development of an Effective Diastereoselective 3+2 Annulation Tactic Exploiting an Aldol/Brook Rearrangement/Cyclization Cascade [O] . Dr. Heeoon Han, Dr. Amos B. Smith III -1

机译：阴离子中继化学：开发利用Aldol / Brook重排/环化级联的有效非对映选择性3 + 2环空策略
6. Formation of Functionalized Carbocycles via Base-Promoted Ring Opening/Brook Rearrangement/Allylic Alkylation of g-Silyl-b, g-epoxybutanenitrile Followed by Nitrile Anion Cyclization with Bis-Electrophiles [O] . -1

机译：通过基促促进的环形开口/芦苇/牛油-B，G-环氧丁丁腈的烯丙基烷基化的官能化碳缩放族的形成，然后用双电热液乙腈环化环化

Formation of Functionalized Carbocycles via Base-Promoted Ring Opening/Brook Rearrangement/Allylic Alkylation of gamma-Silyl-beta,gamma-epoxybutanenitrile Followed by Nitrile Anion Cyclization with Bis-Electrophiles

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