Highly Stereoselective Palladium-Catalyzed [3+2] Cycloaddition of Vinyl Epoxides and N-Benzothiazolimines

被引：13

作者：

Song, Xiaoxiao ^{[1
]}

Gu, Mengjie ^{[1
]}

Chen, Xiaoyun ^{[2
]}

Xu, Lei ^{[1
]}

Ni, Qijian ^{[1
]}

机构：

[1] Anhui Normal Univ, Key Lab Functionalized Mol Solids, Minist Educ,Coll Chem & Mat Sci, Anhui Key Lab Mol Based Mat,State Key Lab Cultiva, Wuhu 241002, Peoples R China

[2] Jiangsu Univ Sci & Technol, Sch Environm & Chem Engn, Zhenjiang 212003, Jiangsu, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 8卷 / 12期

基金：

中国国家自然科学基金;

关键词：

palladium; asymmetric catalysis; cycloaddition; vinyl epoxide; oxazolidine; ENANTIOSELECTIVE CONSTRUCTION; VINYLCYCLOPROPANES; 1,3-OXAZOLIDINES; VINYLOXIRANES; OXIRANES; ROUTE; 3-NITROINDOLES; DERIVATIVES; IMINES; LMINES;

D O I：

10.1002/ajoc.201900636

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric [3+2] cycloaddition of racemic vinyl epoxides with N-benzothiazolimines has been presented under Pd-catalysis. This transformation provides rapid access to highly functionalized oxazolidine scaffolds in generally good yields along with high stereoselectivities (up to 99% ee, 8.5 : 1 d.r.) under mild conditions. The use of chiral BINAP ligand enabled this asymmetric transformation with a broad substrate tolerance.

引用

页码：2180 / 2183

页数：4

共 64 条

[1] Utilizing Palladium-Stabilized Zwitterions for the Construction of N-Heterocycles
Allen, Benjamin D. W.
Lakeland, Christopher P.
Harrity, Joseph P. A.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (56) : 13830 - 13857
[2] [Anonymous], 2018, ANGEW CHEM, V130, P2156
[3] [Anonymous], 2018, ANGEW CHEM, V130, P6407
[4] [Anonymous], 2014, ANGEW CHEM, V126, P6557
[5] Bentley J., 2008, Patent WO, Patent No. [2008/092891 A1, 2008092891]
[6] Stereoselective Synthesis of Fused Vinylcyclopropanes by Intramolecular Tsuji-Trost Cascade Cyclization
Braun, John
Ariens, Maxim I.
Matsuo, Bianca T.
de Vries, Steven
van Wordragen, Ellen D. H.
Ellenbroek, Brecht D.
Vande Velde, Christophe M. L.
Orru, Romano V. A.
Ruijter, Eelco
[J]. ORGANIC LETTERS, 2018, 20 (21) : 6611 - 6615
[7] Pd-Catalyzed Dearomatization of Anthranils with Vinylcyclopropanes by [4+3] Cyclization Reaction
Cheng, Qiang
Xie, Jia-Hao
Weng, Yue-Cheng
You, Shu-Li
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (17) : 5739 - 5743
[8] Stereodivergent Synthesis of Tetrahydrofuroindoles through Pd-Catalyzed Asymmetric Dearomative Formal [3+2] Cycloaddition
Cheng, Qiang
Zhang, Fang
Cai, Yue
Guo, Yin-Long
You, Shu-Li
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (08) : 2134 - 2138
[9] Palladium-Catalyzed Highly Stereoselective Dearomative [3
Cheng, Qiang
Zhang, Hui-Jun
Yue, Wen-Jun
You, Shu-Li
[J]. CHEM, 2017, 3 (03): : 428 - 436
[10] Commons T.J., 2008, PCT Int. Appl, Patent No. [WO2008021338A220080221, 2008021338]

← 1 2 3 4 5 6 7 →