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One-Pot Reductive Allylation of Amides by Using a Combination of Titanium Hydride and an Allylzinc Reagent: Application to a Total Synthesis of (–)-Castoramine
Synlett ( IF 1.7 ) Pub Date : 2018-06-26 , DOI: 10.1055/s-0037-1610435 Hidetoshi Tokuyama 1 , Suguru Itabashi 1 , Masashi Shimomura 1 , Manabu Sato 1 , Hiroki Azuma 1 , Kentaro Okano 1 , Juri Sakata 1
Synlett ( IF 1.7 ) Pub Date : 2018-06-26 , DOI: 10.1055/s-0037-1610435 Hidetoshi Tokuyama 1 , Suguru Itabashi 1 , Masashi Shimomura 1 , Manabu Sato 1 , Hiroki Azuma 1 , Kentaro Okano 1 , Juri Sakata 1
Affiliation
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A one-pot direct reductive allylation protocol has been developed for the synthesis of secondary amines by using titanium hydride and an allylzinc reagent. This protocol is applicable to a broad range of substrates, including acyclic amides, benzamides, α,β-unsaturated amides, and lactams. The stereochemical outcome obtained from the reaction with crotylzinc reagent suggested that the allylation reaction proceeds through a six-membered cyclic transition state. A total synthesis of (–)-castoramine was accomplished by following this protocol for the highly stereoselective construction of contiguous stereocenters.
中文翻译：
使用氢化钛和烯丙基锌试剂的组合对酰胺进行一锅还原烯丙基化：在 (-)-蓖麻胺的全合成中的应用
已经开发了一种使用氢化钛和烯丙基锌试剂合成仲胺的一锅直接还原烯丙基化方案。该协议适用于广泛的底物，包括无环酰胺、苯甲酰胺、α,β-不饱和酰胺和内酰胺。从与巴豆基锌试剂反应获得的立体化学结果表明烯丙基化反应通过六元环过渡态进行。(-)-蓖麻胺的全合成是通过遵循此协议来完成的，用于连续立体中心的高度立体选择性构建。
更新日期：2018-06-26
中文翻译：
使用氢化钛和烯丙基锌试剂的组合对酰胺进行一锅还原烯丙基化：在 (-)-蓖麻胺的全合成中的应用
已经开发了一种使用氢化钛和烯丙基锌试剂合成仲胺的一锅直接还原烯丙基化方案。该协议适用于广泛的底物，包括无环酰胺、苯甲酰胺、α,β-不饱和酰胺和内酰胺。从与巴豆基锌试剂反应获得的立体化学结果表明烯丙基化反应通过六元环过渡态进行。(-)-蓖麻胺的全合成是通过遵循此协议来完成的，用于连续立体中心的高度立体选择性构建。
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