Acetic Acid Mediated Regioselective [3+3] Cycloaddition of Substituted Cyclopropane-1,1-dicarbonitriles with 1,4-Dithiane-2,5-diol

被引：6

作者：

Wan, Xinyi ^{[1
]}

Li, Haiwen ^{[1
]}

Wang, Shan ^{[1
]}

Wang, Cunde ^{[1
]}

机构：

[1] Yangzhou Univ, Sch Chem & Chem Engn, Yangzhou 225002, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 19期

关键词：

DONOR-ACCEPTOR CYCLOPROPANES; RING-OPENING REACTIONS; DIASTEREOSELECTIVE CONSTRUCTION; ANNULATIONS; POTENT; 1,1-DIESTERS; INHIBITORS; ACCESS; TETRAHYDROTHIOPYRANS; DISCOVERY;

D O I：

10.1021/acs.joc.2c01610

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An acetic acid mediated regioselective [3 + 3] cycloaddition of substituted cyclopropane-1,1-dicarbonitriles with in situ generated mercaptoa- cetaldehyde was developed for the synthesis of highly stereoselective tetrahydrothiopyranols. This transformation created two new bonds in a single operation for generating complexity in tetrahydrothiopyrans. This method is characterized by cheap and readily available starting materials, simple operation, and mild reaction conditions.

引用

页码：13375 / 13382

页数：8

共 62 条

[11] Enantioselective and Protecting Group-Free Synthesis of 1-Deoxythionojirimycin, 1-Deoxythiomannojirimycin, and 1-Deoxythiotalonojirimycin [J].

Gunasundari, Thanikachalam ;

Chandrasekaran, Srinivasan .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (19) :6685-6688

[12] Synthesis of Functionalized 2-Aminopyrroles by Lewis Acid Catalyzed Ring-opening of 1,1,2,3-Tetrasubstituted Cyclopropanes with Arylamines [J].

Han Ying ;

Fu Qin ;

Tang Wanquan ;

Yan Chaoguo .

CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (08) :1867-1872

[13] A highly efficient In(OTf)3-catalyzed [3+3] annulation of spirocyclopropyl oxindoles with 1,4-di-thiane-2,5-diol [J].

Hao, Yongjia ;

Gong, Yi ;

Cao, Zhongyan ;

Zhou, Ying ;

Zhou, Jian .

CHINESE CHEMICAL LETTERS, 2020, 31 (03) :681-684

[14]

Hegab MI, 2021, INDIAN J CHEM B, V60, P1502

[15] PCl5-mediated ring-openings of trans-2,3-disubstituted cyclopropane-1,1-diesters: A stereoselective way to trisubstituted vinyl chlorides [J].

Hua, Deju ;

Yang, Pengfei ;

Shen, Yue ;

Yang, Gaosheng ;

Chai, Zhuo .

TETRAHEDRON, 2017, 73 (08) :1205-1210

[16]

Kakinuma H, 2009, Jpn. Kokai Tokkyo Koho, Patent No. 2009167103

[17] (1S)-1,5-Anhydro-1-[5-(4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio-D-glucitol (TS-071) is a Potent, Selective Sodium-Dependent Glucose Cotransporter 2 (SGLT2) Inhibitor for Type 2 Diabetes Treatment [J].

Kakinuma, Hiroyuki ;

Oi, Takahiro ;

Hashimoto-Tsuchiya, Yuko ;

Arai, Masayuki ;

Kawakita, Yasunori ;

Fukasawa, Yoshiki ;

Iida, Izumi ;

Hagima, Naoko ;

Takeuchi, Hiroyuki ;

Chino, Yukihiro ;

Asami, Jun ;

Okumura-Kitajima, Lisa ;

Io, Fusayo ;

Yamamoto, Daisuke ;

Miyata, Noriyuki ;

Takahashi, Teisuke ;

Uchida, Saeko ;

Yamamoto, Koji .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (08) :3247-3261

[18] I2/K2CO3-promoted ring-opening/cyclization/rearrangement/aromatization sequence: A powerful strategy for the synthesis of polysubstituted furans [J].

Liu, Jia-Ming ;

Liu, Xing-Yu ;

Qing, Xu-Shun ;

Wang, Ting ;

Wang, Cun-De .

CHINESE CHEMICAL LETTERS, 2017, 28 (02) :458-462

[19] DBU-mediated [4+2] annulations of donoracceptor cyclopropanes with 3-aryl-2-cyanoacrylates for the synthesis of fully substituted anilines [J].

Liu, Jiaming ;

Qian, Siran ;

Su, Zhenjie ;

Wang, Cunde .

RSC ADVANCES, 2017, 7 (61) :38342-38349

[20] Solvent-Free DABCO-Mediated [3+2] Cycloadditions of Donor-Acceptor Cyclopropanes with Aldehydes: Strategy for Synthesis of Fully Substituted Furans [J].

Liu, Jiaming ;

Ye, Weijian ;

Qng, Xushun ;

Wang, Cunde .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (17) :7970-7976

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