铜催化 γ-C ((sp3) -H 乳酸化和免疫乳酸化
Tao Sheng1, Zhe Zhuang1, Zhihan Zhao1
1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
这项研究引入了一种新的铜催化方法,用于从托西尔保护的胺中合成g-lactams和g-iminolactones. 反应提供可切换的选择性和获取多样化,生物相关的化学结构.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
背景情况:
- 对罗利丁合成的γ-乳酸化反应具有挑战性,特别是对阿利法胺.
- 使用循环金属化,C-H插入或基C-H抽象的现有方法具有局限性.
研究的目的:
- 开发一种实用且高效的铜催化方法,用于酸胺的γ-C(sp3)-H乳化和iminolactonization.
- 为了实现g-lactams和g-iminolactones之间可切换的选择性.
- 为了合成结构上不同的乳和伊米诺.
主要方法:
- 用铜催化的 γ-C ((sp3) -H 功能化对托西尔保护的阿里法性胺.
- 使用Selectfluor作为唯一的氧化剂.
- 采用两组不同的反应条件来控制选择性.
主要成果:
- 成功实现了用铜催化的γ-乳酸化和iminolactonization.
- 对于 γ-乳酸或 γ-胺基氨酸,已显示可切换的选择性.
- 合成了各种各样的螺旋,合和桥接乳/iminolactones以及isoindolinones.
- 展示了进一步的衍生物化成 γ-氨基酸, δ-氨基醇和罗利丁.
结论:
- 开发了一种通用且实用的方法,用于获取γ-乳酸盐和γ-胺氨酸.
- 该方法为生物重要分子提供了有价值的合成中间体.
- 为罗利丁合成和相关异环循环提供了一种新策略.
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