Stereoselective Synthesis of Contiguous Cyclopropylaziridines: Enabling the Construction of Versatile Chiral Molecules Including γ-Lactams via Ring-Opening Reactions

被引：1

作者：

Han, Jiho ^{[1
]}

Ha, Hyun-Joon ^{[1
]}

Yang, Jung Woon ^{[2
]}

机构：

[1] Hankuk Univ Foreign Studies, Dept Chem, Yongin 17035, South Korea

[2] Sungkyunkwan Univ, Dept Energy Sci, 16419, Suwon, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 12期

基金：

新加坡国家研究基金会;

关键词：

Contiguous cyclopropylaziridine; Stereo-selective synthesis; Chiral building block; Cyclo-propanation; Organocatalysis; DONOR-ACCEPTOR CYCLOPROPANES; ENANTIOSELECTIVE CYCLOPROPANATION; ORGANOCATALYTIC CYCLOPROPANATION; ALKYLATION REACTIONS; DERIVATIVES; CHEMISTRY; AZIRIDINE; CATALYSIS; HYBRIDS;

D O I：

10.1002/adsc.202300177

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The synthesis of chiral contiguous cyclopropylaziridine was achieved through cyclopropanation of (E)-3-((S)-1-[(R)-1-phenylethyl)aziridin-2-yl]acrylaldehyde with bromomalonate in the presence of (2R)- or (2S)-[diphenyl(trimethylsilyloxy) methyl]pyrrolidine as a chiral organocatalyst and 2,6-lutidine as a base. This chiral cyclopropylaziridine was then subjected to various functional transformations, leading to the construction of a wide range of structurally important motifs.

引用

页码：1970 / 1976

页数：7

共 19 条

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[2] Synthesis of Novel Sustainable Oligoamides Via Ring-Opening Polymerization of Lactams Based on (-)-Menthone
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[3] A stereoselective synthesis of a key intermediate to 1β-methylcarbapenem via aziridine ring-opening reaction
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[6] Recent advances in the application of contiguously functionalized aziridines for the synthesis of pharmaceutical precursors via regioselective ring-opening reactions
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