Copper-Catalyzed Regio- and Stereoselective Ring-Opening of Cyclic Sulfamidates with Grignard Reagents assisted by Lithium Chloride

被引：10

作者：

Arigala, Pitchaiah ^{[1
]}

Sadu, Venkata S. ^{[2
]}

Hwang, In-Taek ^{[1
]}

Hwang, Jin-Soo ^{[1
]}

Kim, Chul-Ung ^{[1
]}

Lee, Kee-In ^{[1
,2
]}

机构：

[1] Korea Res Inst Chem Technol, Green Chem Div, Taejon 305600, South Korea

[2] Univ Sci & Technol, Dept Green Chem & Environm Biotechnol, Taejon 305333, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 09期

关键词：

CuI/LiCl; inversion; ring-opening; sulfamidate; alpha-branched benzylamine; CROSS-COUPLING REACTIONS; ASYMMETRIC-SYNTHESIS; ALKYL-HALIDES; TERT-BUTANESULFINAMIDE; PHOTOREDOX CATALYSIS; EFFICIENT SYNTHESIS; CHIRAL AZIRIDINES; AMINO-ACIDS; ARYLATION; SECONDARY;

D O I：

10.1002/adsc.201400850

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Copper-catalyzed ring-opening reactions of cyclic 1,2-sulfamidates with a wide range of Grignard reagents have been investigated. The use of lithium chloride as an additive is essential to activate C-O bond cleavage. The reaction represents highly regio- and stereoselective, and thus allows for efficient synthesis of enantioenriched alpha-branched benzylamine derivatives. Furthermore, we demonstrated that the products are potential to be used as building blocks for the preparation of wide range of nitrogen-containing heterocycles.

引用

页码：2027 / 2032

页数：6

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