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
收藏
页码：13375 / 13382
页数：8
相关论文
共 62 条
[1]  
Barberousse V., 2008, Patent No. [2906248A120080328, 29062481200803]
[2]   Diastereoselective Synthesis of Substituted Tetrahydrothiopyrans via (3,5)-Thionium-Ene Cyclization Reaction [J].
Bondalapati, Somasekhar ;
Gogoi, Paramartha ;
Indukuri, Kiran ;
Saikia, Anil K. .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (05) :2508-2512
[3]   Ring Opening of Donor-Acceptor Cyclopropanes with N-Nucle-ophiles [J].
Budynina, Ekaterina M. ;
Ivanov, Konstantin L. ;
Sorokin, Ivan D. ;
Melnikov, Mikhail Ya. .
SYNTHESIS-STUTTGART, 2017, 49 (14) :3035-3068
[4]   Intramolecular donor-acceptor cyclopropane ring-opening cyclizations [J].
Cavitt, Marchello A. ;
Phun, Lien H. ;
France, Stefan .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (03) :804-818
[5]  
Chatterjee S. S., 2001, Ger. Offen., Patent No. [19954569A120010517, 19954569120010]
[6]   Domino Synthetic Strategy for Tetrahydrothiopyran Derivatives from Benzaldehydes, 2-Acetylfuran/2-Acetylthiophene, and Sodium Sulfide [J].
Chen, Dongdong ;
Du, Weixia ;
Yang, Xufeng ;
Liu, Tao .
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (14) :9088-9095
[7]  
Chu H., 2021, International Patent Application Publication, Patent No. 2021096860
[8]   FeCl3-Promoted [3+2] Annulations of γ-Butyrolactone Fused Cyclopropanes with Heterocumulenes [J].
Feng, Manli ;
Yang, Pengfei ;
Yang, Gaosheng ;
Chen, Wenlong ;
Chai, Zhuo .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01) :174-184
[9]   Catalytic asymmetric [3+3] annulation of cyclopropanes with mercaptoacetaldehyde [J].
Fu, Xuan ;
Lin, Lili ;
Xia, Yong ;
Zhou, Pengfei ;
Liu, Xiaohua ;
Feng, Xiaoming .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (25) :5914-5917
[10]   Carbocycles from donor-acceptor cyclopropanes [J].
Grover, Huck K. ;
Emmett, Michael R. ;
Kerr, Michael A. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (03) :655-671
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