A Novel Method for the Chlorolactonization of Alkenoic Acids Using Diphenyl Sulfoxide/Oxalyl Chloride

被引:19
作者
Ding, Rui [1 ]
Lan, Liyuan [1 ]
Li, Shuhui [1 ]
Liu, Yongguo [1 ]
Yang, Shaoxiang [1 ]
Tian, Hongyu [1 ]
Sun, Baoguo [1 ]
机构
[1] Beijing Technol & Business Univ, Beijing Key Lab Flavor Chem, Beijing Adv Innovat Ctr Food Nutr & Human Hlth, Beijing 100048, Peoples R China
来源
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 13期
关键词
chlorolactonization; alkenoic acids; diphenyl sulfoxide; oxalyl chloride; chlorodiphenylsulfonium salt; UNSATURATED-ACIDS; HYDROGEN-PEROXIDE; SODIUM-BROMIDE; ASYMMETRIC CHLOROLACTONIZATION; CARBOXYLIC-ACIDS; BROMOLACTONIZATION; IODOLACTONIZATION; HALOLACTONIZATION; BROMINATION; ACTIVATION;
D O I
10.1055/s-0037-1609687
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile chlorolactonization of alkenoic acids by treatment with diphenyl sulfoxide/oxalyl chloride has been developed. The reaction can generate various chlorolactones in moderate to good yields, wherein the chlorodiphenylsufonium salt derived from diphenyl sulfoxide/oxalyl chloride serves as the source of Cl+.
引用
收藏
页码:2555 / 2566
页数:12
相关论文
共 37 条
[21]   Synthesis of chlorinated β- and γ-lactones from unsaturated acids with sodium hypochlorite and Lewis acids [J].
Lopez-Lopez, Jose A. ;
Guerra, Francisco M. ;
Moreno-Dorado, F. Javier ;
Jorge, Zacarias D. ;
Massanet, Guillermo M. .
TETRAHEDRON LETTERS, 2007, 48 (10) :1749-1752
[22]   Selenium-catalyzed halolactonization: Nucleophilic activation of electrophilic halogenating reagents [J].
Mellegaard, SR ;
Tunge, JA .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (25) :8979-8981
[23]   Selenium-catalyzed oxidative halogenation [J].
Mellegaard-Waetzig, Shelli R. ;
Wang, Chao ;
Tunge, Jon A. .
TETRAHEDRON, 2006, 62 (30) :7191-7198
[24]   RECENT PROGRESS IN ORGANOCATALYTIC ASYMMETRIC HALOCYCLIZATION [J].
Murai, Kenichi ;
Fujioka, Hiromichi .
HETEROCYCLES, 2013, 87 (04) :763-+
[25]   Enantioselective Bronsted Acid-Catalyzed N-Acyliminium Cyclization Cascades [J].
Muratore, Michael E. ;
Holloway, Chloe A. ;
Pilling, Adam W. ;
Storer, R. Ian ;
Trevitt, Graham ;
Dixon, Darren J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) :10796-+
[26]   Asymmetric Iodolactonization: An Evolutionary Account [J].
Nolsoe, Jens M. J. ;
Hansen, Trond V. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (15) :3051-3065
[27]   Halo- and selenolactonisation: the two major strategies for cyclofunctionalisation [J].
Ranganathan, S ;
Muraleedharan, KM ;
Vaish, NK ;
Jayaraman, N .
TETRAHEDRON, 2004, 60 (25) :5273-5308
[28]  
Stobbe H, 1902, LIEBIGS ANN CHEM, V321, P83
[29]   Regioselective reactions on a 1,3-disubstituted dihydroxymethyl or dicarboxyl hexahydropentalene skeleton [J].
Tanase, Constantin I. ;
Draghici, Constantin ;
Shova, Sergiu ;
Cojocaru, Ana ;
Maganu, Maria ;
Munteanu, Cristian V. A. ;
Cocu, Florea .
TETRAHEDRON, 2015, 71 (38) :6852-6859
[30]   An Organocatalytic Asymmetric Chlorolactonization [J].
Whitehead, Daniel C. ;
Yousefi, Roozbeh ;
Jaganathan, Arvind ;
Borhan, Babak .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (10) :3298-+