Site-selective, catalytic, and diastereoselective sp3 C–H hydroxylation and alkoxylation of vicinally functionalized lactams

Timothy K. Beng; Victoria Shearer; Rachel Davey; Ivianne Redman

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Site-selective, catalytic, and diastereoselective sp3 C–H hydroxylation and alkoxylation of vicinally functionalized lactams

机译：基地选择，催化和非对映选择性SP3 C-H羟基化和邻官能化内酰胺的烷氧基化

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The C–H bond functionalization of sp ~(3) carbon centres presents a significant challenge due to the inert nature of hydrocarbons as well as the need to selectively functionalize one of the numerous aliphatic C–H bonds embodied in organic molecules. Here, we describe catalytic, diastereoselective, and site-selective sp ~(3) C–H hydroxylation/alkoxylation protocols featuring dihydroisoquinolones, γ-, and δ-lactams, which bear vicinal stereocenters. The hydroxylation strategy utilizes oxygen, a waste-free oxidant and affords attractive fragments for potential drug discovery. Fe-catalyzed dehydrative coupling of the resulting tertiary alcohols with simple primary alcohols has led to the construction of highly versatile unsymmetrical dialkyl ethers.

机译：SP〜（3）碳中心的C-H键官能化由于烃的惰性性质以及需要选择性地官能化有机分子中体现的许多脂族C-H键之一的需要进行显着挑战。在这里，我们描述了具有二羟异喹啉，γ-和δ-内酰胺的催化，非对映选择性和位点选择性SP〜（3）C-H羟基化/烷氧基化方案，其承受邻近立体封闭物。羟基化策略利用氧气，无氧化氧化剂，并为潜在的药物发现提供有吸引力的碎片。由此产生的叔醇的Fe催化的脱水偶联具有简单的初级醇导致了高度通用的非对称二烷基醚的结构。

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《RSC Advances》 |2020年第34期|共8页
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Timothy K. Beng; Victoria Shearer; Rachel Davey; Ivianne Redman;
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1. Site-selective, catalytic, and diastereoselective sp(3)C-H hydroxylation and alkoxylation of vicinally functionalized lactams [J] . Beng Timothy K., Shearer Victoria, Davey Rachel, RSC Advances . 2020,第34期

机译：位点选择，催化和非对映选择性SP（3）C-H羟基化和邻官能官能化内酰胺的烷氧基化
2. CAN mediated decarboxylative hydroxylation/alkoxylation of N-aryl-gamma-lactam-carboxylic acids at room temperature:an easy access to N-aryl-alpha-hydroxy/alkoxy-gamma-lactams [J] . Pranab Haldar, Jayanta K.Ray Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2008,第22期

机译：CAN介导的N-芳基-γ-内酰胺羧酸在室温下的脱羧羟基化/烷氧基化：易于获得N-芳基-α-羟基/烷氧基-γ-内酰胺
3. A direct and vicinal functionalization of the 1-methyl-2-quinolone framework: 4-alkoxylation and 3-chlorination [J] . Feiyue Hao, Haruyasu Asahara, Nagatoshi Nishiwaki Organic & biomolecular chemistry . 2016,第22期

机译：1-甲基-2-喹诺酮骨架的直接和邻位官能化：4-烷氧基化和3-氯化
4. Diastereoselective hydroxylation of piperidinones.An experiment synthesis of (2S,5R)-50hydroxylysine [C] . Gilles Guichard, Julien Marin, Claude Didierjean, European Peptide Symposium . 2002

机译：哌啶酮的非对映选择性羟基化。实验合成（2S，5R）-50羟基碱基
5. Part I. The use of covalently attached synthetic metalloporphyrins in the remote site-selective hydroxylation of steroids. Part II. The use of ionically coordinated metalloporphyrins in the remote site-selective hydroxylation of steroids. [D] . Stuk, Timothy Lee. 1991

机译：第一部分共价连接的合成金属卟啉在类固醇的远程部位选择性羟基化中的用途。第二部分离子配位的金属卟啉在类固醇的远程位点选择性羟基化中的使用。
6. Diastereoselective synthesis of vicinal tertiary and N-substituted quaternary stereogenic centers by catalytic hydroalkylation of dienes [O] . Matthew J. Goldfogel, Simon J. Meek 2016

机译：通过二烯催化加氢烷基化非必须地合成邻位叔和N-取代的季位立体中心
7. Silver-Promoted Site-Selective Intramolecular Cyclization of 2-Methylthiobenzamide Through α-C(sp3)–H Functionalization [O] . Ke Yang, Ben Niu, Zhiyan Ma, 2019

机译：通过α-C（SP3）-H官能化2-甲基硫苯胺的银促进的位点选择性分子化环化

Site-selective, catalytic, and diastereoselective sp3 C–H hydroxylation and alkoxylation of vicinally functionalized lactams

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