Diastereoselective Synthesis of N-Heterocycle Substituted Cyclobutanes via Michael Addition onto Cyclobutenes

被引：0

作者：

Robert, Emma G. L. ^{[1
]}

Waser, Jerome ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Inst Sci & Ingn Chim, Lab Catalysis & Organ Synth, CH-1015 Lausanne, Switzerland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2025年 / 31卷 / 08期

基金：

瑞士国家科学基金会;

关键词：

Michael addition; Cyclobutanes; Cyclobutenes; Diastereoselectivity; Small ring systems; DERIVATIVES; PEPTIDES; POTENT; ACIDS;

D O I：

10.1002/chem.202403986

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we present a method for the diastereoselective synthesis of N-heterocycle-substituted cyclobutanes from commercially available bromocyclobutanes. This method enables the efficient formation of various heterocyclic aminocyclobutane esters and amides using simple reagents. Notably, N-nucleophiles such as imidazoles, azoles, and nucleobase derivatives were successfully incorporated, enhancing the chemical diversity of small ring building blocks for medicinal chemistry applications.

引用

页数：5

共 50 条

[1] Manganese(III) reactions in N-heterocycle synthesis:: The preparation of substituted pyrrolidinones
Davies, DT
Kapur, N
Parsons, AF
TETRAHEDRON LETTERS, 1998, 39 (24) : 4397 - 4400
[2] N-Heterocycle construction via cyclic sulfamidates. Applications in synthesis
Bower, John F.
Rujirawanicha, Janjira
Gallagher, Timothy
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (07) : 1505 - 1519
[3] Synthesis of N-Heterocycle Substituted Silyl Ligands within the Coordination Sphere of Iron
Witteman, Leon
Lutz, Martin
Moret, Marc-Etienne
ORGANOMETALLICS, 2018, 37 (18) : 3024 - 3034
[4] Copper(I) reactions in N-heterocycle synthesis:: efficient preparation of substituted pyrrolidinones
Davies, DT
Kapur, N
Parsons, AF
TETRAHEDRON LETTERS, 1999, 40 (49) : 8615 - 8618
[5] α-Diazo oxime ethers for N-heterocycle synthesis
Choi, Subin
Ha, Sujin
Park, Cheol-Min
CHEMICAL COMMUNICATIONS, 2017, 53 (45) : 6054 - 6064
[6] Synthesis, structure and fluorescence of copper(II) complex with substituted aroylhydrazone and monodentate N-heterocycle
Liu Hui-Yan
Wang Hai-Ying
Niu De-Zhong
Lu Zai-Sheng
CHINESE JOURNAL OF INORGANIC CHEMISTRY, 2007, 23 (04) : 611 - 614
[7] Towards the synthesis of N-heterocycle containing BINOL-phosphoramidites
Recsei, Carl
McErlean, Christopher S. P.
TETRAHEDRON-ASYMMETRY, 2010, 21 (02) : 149 - 152
[8] Symmetrically Substituted Zinc Phthalocyanine Derivatives Bearing N-heterocycle Moieties Synthesis and structural analysis investigations
Youssef, Tamer E.
Al-Turaif, Hamad
Baleanu, Dumitru
REVISTA DE CHIMIE, 2014, 65 (11): : 1266 - 1270
[9] NBS-Promoted C-H Amination of Enaminones for the Synthesis of N-Heterocycle Substituted Enaminones**
Duan, Xiyan
Li, Huimin
Li, Weinan
Wang, Junqi
Liu, Ning
CHEMISTRYSELECT, 2021, 6 (25): : 6478 - 6482
[10] Diastereoselective Synthesis of Highly Functionalized γ-Lactams via Ugi Reaction/Michael Addition
Vidal, Herika D. A.
Nunes, Paulo S. G.
Martinez, Alice K. A.
Januario, Marcelo A. P.
Santiago, Pedro H. O.
Ellena, Javier
Correa, Arlene G.
CHEMISTRY-AN ASIAN JOURNAL, 2025, 20 (01)

← 1 2 3 4 5 →