Manganese-catalyzed ring-opening chlorination of cyclobutanols: regiospecific synthesis of γ-chloroketones

被引：51

作者：

Huan, Leitao ^{[1
]}

Zhu, Chen ^{[1
,2
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, 199 Ren Ai Rd, Suzhou 215123, Jiangsu, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2016年 / 3卷 / 11期

基金：

中国国家自然科学基金;

关键词：

C BOND-CLEAVAGE; QUATERNARY STEREOGENIC CENTERS; BAYLIS-HILLMAN REACTION; CARBON-CARBON BONDS; TERT-CYCLOBUTANOLS; H FLUORINATION; TITANIUM(IV) CHLORIDE; ASYMMETRIC ARYLATION; BETA-KETOESTERS; KETONES;

D O I：

10.1039/c6qo00443a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We disclose an efficient manganese-catalyzed ring-opening chlorination of cyclobutanols. This reaction has a broad substrate scope, affording a variety of gamma-chloro alkyl ketones and medium-sized benzocyclic chlorides in synthetically useful yields and unique regioselectivities. The merits including mild reaction conditions and employment of inexpensive catalysts and reagents make it a practical approach for the production of gamma-chlorinated ketones.

引用

页码：1467 / 1471

页数：5

共 70 条

[1] Regio- and Stereoselective Ring Opening of Enantiomerically Enriched 2-Aryl Oxetanes and 2-Aryl Azetidines with Aryl Borates [J].

Bertolini, Ferruccio ;

Crotti, Stefano ;

Di Bussolo, Valeria ;

Macchia, Franco ;

Pineschi, Mauro .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :8998-9007

[2] Synthesis of γ-halogenated ketones via the Ce(IV)-mediated oxidative coupling of cyclobutanols and inorganic halides [J].

Casey, Brian M. ;

Eakin, Cynthia A. ;

Flowers, Robert A., II .

TETRAHEDRON LETTERS, 2009, 50 (12) :1264-1266

[3] Synthesis and SAR investigations for novel melanin-concentrating hormone 1 receptor (MCH1) antagonists part 2:: A hybrid strategy combining key fragments of HTS hits [J].

Chen, Chien-An ;

Jiang, Yu ;

Lu, Kai ;

Daniewska, Irena ;

Mazza, Christine G. ;

Negron, Leonardo ;

Forray, Carlos ;

Parola, Tony ;

Li, Boshan ;

Hegde, Laxminarayan G. ;

Wolinsky, Toni D. ;

Craig, Douglas A. ;

Kong, Ron ;

Wetzel, John M. ;

Andersen, Kim ;

Marzabadi, Mohammad R. .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (16) :3883-3890

[4] Recent Advances in Transition-Metal-Catalyzed Functionalization of Unstrained Carbon-Carbon Bonds [J].

Chen, Feng ;

Wang, Teng ;

Jiao, Ning .

CHEMICAL REVIEWS, 2014, 114 (17) :8613-8661

[5] AN IMPROVED SYNTHESIS OF CYCLOPROPYL PHENYL KETONE AND RELATED SUBSTANCES [J].

CLOSE, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (06) :1455-1458

[6] THE ORGANOMETALLIC CHEMISTRY OF ALKANES [J].

CRABTREE, RH .

CHEMICAL REVIEWS, 1985, 85 (04) :245-269

[7] Reinvestigation of a Catalytic, Enantioselective Alkene Dibromination and Chlorohydroxylation [J].

Denmark, Scott E. ;

Carson, Nessa .

ORGANIC LETTERS, 2015, 17 (23) :5728-5731

[8] Direct activation of relatively unstrained carbon-carbon bonds in homogeneous systems [J].

Dermenci, Alpay ;

Coe, Jotham W. ;

Dong, Guangbin .

ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (05) :567-581

[9] THE BINARY REAGENT PHSECL-ZNCL2 - A POWERFUL CHLORO-PHENYLSELENENYLATING AGENT OF ELECTROPHILIC OLEFINS [J].

DONOFRIO, F ;

PARLANTI, L ;

PIANCATELLI, G .

TETRAHEDRON LETTERS, 1995, 36 (11) :1929-1932

[10] METHODS FOR THE INTRODUCTION OF A PHENYLSELENIUM DICHLORIDE GROUP INTO THE ALPHA-POSITION OF CARBONYL-COMPOUNDS - SYNTHESES OF ENONES [J].

ENGMAN, L .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4031-4037

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