Cy-SaBOX/Copper(II)-Catalyzed Highly Diastereo- and Enantioselective Synthesis of Bicyclic N,O Acetals

被引：44

作者：

Liu, Qiong-Jie ^{[1
]}

Wang, Lijia ^{[1
]}

Kang, Qi-Kai ^{[1
]}

Zhang, X. Peter ^{[3
]}

Tang, Yong ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China

[3] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 32期

基金：

美国国家科学基金会; 中国国家自然科学基金;

关键词：

asymmetric catalysis; copper; cycloaddition; heterocycles; X-ray diffraction; HETERO-DIELS-ALDER; INVERSE-ELECTRON-DEMAND; BETA; GAMMA-UNSATURATED ALPHA-KETOESTERS; CATALYTIC ASYMMETRIC-SYNTHESIS; DONOR-ACCEPTOR CYCLOPROPANES; MICHAEL ADDITION; INTRAMOLECULAR CYCLOPROPANATION; AMARYLLIDACEAE ALKALOIDS; PENICILLIUM-CITRINUM; THREEFOLD SYMMETRY;

D O I：

10.1002/anie.201603911

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Facile and effective access for the asymmetric construction of the useful and important skeleton of the bicyclic N,O-acetals is described. Cu-II/SaBOX could catalyze the reaction of beta,gamma-unsaturated alpha-ketoesters with cyclic enamines efficiently, thus affording the desired products in excellent yields with excellent stereoselectivities (21 examples; up to 99% yields; up to > 95: 5 d.r.; and 95-99% ee). This reaction can be well performed on gram scale, even with only 1 mol% catalyst loading. The single-crystal structures of the copper complexes lead to a good understanding of the stereosynergistic effects of the sidearm.

引用

页码：9220 / 9223

页数：4

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