B(C6F5)3-catalyzed regio- and stereoselective cyanation of isatogens and their derivatives

被引：3

作者：

Sakai, Ryoka ^{[3
]}

Ishihara, Nanaka ^{[2
]}

Harada, Shinji ^{[1
,2
,4
]}

Arai, Shigeru ^{[2
,4
]}

机构：

[1] Chiba Univ, Inst Adv Acad Res, 1-33 Yayoi Cho,Inage Ku, Chiba 2638522, Japan

[2] Chiba Univ, Grad Sch Pharmaceut Sci, 1-8-1 Inohana,Chuo Ku, Chiba 2608675, Japan

[3] Chiba Univ, Fac Pharmaceut Sci, 1-8-1 Inohana, Chuo ku, Chiba 2608675, Japan

[4] Chiba Univ, Mol Chiral Res Ctr, 1-33 Yayoi Cho,Inage Ku, Chiba 2638522, Japan

来源：

TETRAHEDRON LETTERS | 2024年 / 137卷

基金：

日本学术振兴会;

关键词：

Catalysis; Cyanation; Stereoselective; Lewis acid; CATALYTIC ENANTIOSELECTIVE CYANOSILYLATION; ONE-POT; OXIDATIVE REARRANGEMENT; ACCESS; INDOLIN-3-ONES; CYCLOADDITION; ACTIVATION; ALDEHYDES; INDOLES; BOND;

D O I：

10.1016/j.tetlet.2024.154909

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we report the regioselective cyanation of isatogen (3-indolone N-oxide) and its derivatives. The high electrophilicity of isatogen is a key feature for their various chemical transformations, and we describe a new application to use boron catalyst for regio- and stereoselective cyanation at C2 position of isatogen. The combination of B(C6F5)3 and Me3SiCN is optimal, and the C2-cyano adducts are exclusively obtained in up to quantitative yield. In addition, isatogenol that includes a tertiary hydroxyl group at C3 position is also suitable for this cyanation to create consecutive tetra-substituted carbons with high stereoselectivity.

引用

页数：4

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