Synthesis of 2-carboxylated aza-ring derivatives through α-monohalogenation/ring-contraction of N-sulfonyl lactams

被引：7

作者：

Sirindil, Fatih ^{[1
]}

Miaskiewicz, Solene ^{[1
]}

Kern, Nicolas ^{[1
]}

Lalaut, Arno ^{[1
]}

Felten, Anne-Sophie ^{[1
]}

Weibel, Jean-Marc ^{[1
]}

Pale, Patrick ^{[1
]}

Blanc, Aurelien ^{[1
]}

机构：

[1] Univ Strasbourg, CNRS, Lab Synth Reactivite Organ & Catalyse, Inst Chim,UMR 7177, 4 Rue Blaise Pascal, F-67070 Strasbourg, France

来源：

TETRAHEDRON | 2017年 / 73卷 / 34期

关键词：

Monohalogenation; Ring-contraction; N-Sulfonyl lactams; 2-Carboxylate aza-rings; MUGINEIC ACID; IRON; CHEMISTRY;

D O I：

10.1016/j.tet.2017.06.067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Carboxylated aza-rings have been synthesized in two steps through a highly selective mono halogenation of N-sulfonylated lactams of various ring sizes (from 5- to 8-membered rings) followed by a ring contraction reaction. The selective monohalogenation of N-sulfonyl lactams has been achieved in modest to excellent yields (9 examples, 39-96%) using N-halogenosuccinimides via the in situ generation of trimethylsilyl ketene aminal derivatives. The so-obtained alpha-halogeno N-sulfonyl lactams were engaged in a ring opening/ring closing reaction in the presence of various alcohols or anilines under basic conditions affording 2-carboxylated aza-rings, such as azetidine, pyrrolidine or piperidine derivatives in high yields (24 examples, 61-99%). (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：5096 / 5106

页数：11

共 16 条

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