3,3-Dimethoxypropylsulfonyl Group: A new versatile protecting and activating group for amine synthesis

被引：3

作者：

Sakamoto, Izumi ^{[1
]}

Iwaoka, Kazuya ^{[1
]}

Kawada, Yuta ^{[1
]}

Naito, Takanori ^{[1
]}

Makida, Kazuyoshi ^{[1
]}

Takeuchi, Yuki ^{[1
]}

Nishii, Takeshi ^{[1
]}

Horikawa, Mitsuyo ^{[1
]}

Kaku, Hiroto ^{[1
]}

Tsunoda, Tetsuto ^{[1
]}

机构：

[1] Tokushima Bunri Univ, Fac Pharmaceut & Sci, Yamashiro Cho, Tokushima, Tokushima 7708514, Japan

来源：

TETRAHEDRON | 2018年 / 74卷 / 24期

关键词：

Amines; Mitsunobu reaction; Phosphorane; Protecting group; Sulphonamide; MITSUNOBU-TYPE ALKYLATION; SECONDARY-AMINES; REAGENTS;

D O I：

10.1016/j.tet.2018.04.088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3,3-Dimethoxypropylsulfonyl (Dimps) chloride was prepared and used as a new versatile sulfonating agent for ammonia, primary and secondary amines to afford corresponding Dimps-amides in excellent yields. The resulting N-nonsubstituted and N-monosubstituted Dimps-amides, activated amines, were alkylated satisfactorily under new Mitsunobu conditions. The Dimps group was removed by treatment in aqueous solution under acidic followed by basic conditions. Furthermore, epilachnene, the defensive droplets from the Mexican bean beetle, Epilachna varivestis, was synthesized utilizing this Dimps methodology in short steps. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：3052 / 3060

页数：9

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