Highly Controlled Ring-Opening of Siloxydifluorocyclopropanes: A Versatile Route to Cyclic Fluoroketones

被引：37

作者：

Kageshima, Yoshiya ^{[1
]}

Suzuki, Chiharu ^{[1
]}

Oshiro, Kojun ^{[1
]}

Amii, Hideki ^{[1
]}

机构：

[1] Gunma Univ, Grad Sch Sci & Technol, Div Mol Sci, Kiryu, Gunma 3768515, Japan

来源：

SYNLETT | 2015年 / 26卷 / 01期

基金：

日本科学技术振兴机构;

关键词：

fluorine; silicon; cyclopropane; ring-opening; ketone; ORGANIC FLUORINE-COMPOUNDS; GEM-DIFLUOROCYCLOPROPANE DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; DIFLUOROCARBENE SOURCE; REARRANGEMENT; KETONES; CYCLOPROPANES; NUCLEOPHILES; EQUIVALENT; ALCOHOLS;

D O I：

10.1055/s-0034-1379599

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient access to cyclic fluoroketones that involves base-promoted ring-opening of siloxydifluorocyclopropanes is presented. Selective formation of gem-difluorinated cycloalkanones and monofluorinated enones has been achieved.

引用

页码：63 / 66

页数：4

共 43 条

[1]

Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine, DOI 10.1002/9780470281895

[2] Solvent effect on intramolecular hydrogen bonds in push-pull conjugated molecules [J].

Bouchy, A ;

Rinaldi, D ;

Rivail, JL .

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2004, 96 (03) :273-281

[3] Fluorinated carbenes [J].

Brahms, DLS ;

Dailey, WP .

CHEMICAL REVIEWS, 1996, 96 (05) :1585-1632

[4] Structure, synthesis, and chemical reactions of fluorinated cyclopropanes and cyclopropenes [J].

Dolbier, WR ;

Battiste, MA .

CHEMICAL REVIEWS, 2003, 103 (04) :1071-1098

[5] THERMAL REARRANGEMENT OF 2,2-DIFLUOROVINYLCYCLOPROPANE - A CONCERTED PATHWAY [J].

DOLBIER, WR ;

ALSADER, BH ;

SELLERS, SF ;

KORONIAK, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2138-2139

[6] FLUORO ANALOGA OF CYCLOHEPTADIENE PHEROMONES OF MARINE BROWN-ALGAE - EXCEPTIONALLY FACILE [3,3]-SIGMATROPIC REARRANGEMENT OF A TRANS-DI(ALKENYL)-SUBSTITUTED GEMINAL DIFLUOROCYCLOPROPANE [J].

ERBES, P ;

BOLAND, W .

HELVETICA CHIMICA ACTA, 1992, 75 (03) :766-772

[7]

Gouverneur V., 2012, Fluorine in Pharmaceutical and Medicinal Chemistry: from biophysical aspects to clinical applications

[8]

Hiyama T., 2013, ORGANOFLUORINE COMPO

[9] Selective difluoromethylation and monofluoromethylation reactions [J].

Hu, Jinbo ;

Zhang, Wei ;

Wang, Fei .

CHEMICAL COMMUNICATIONS, 2009, (48) :7465-7478

[10] CATALYTIC HYDROGENOLYSIS OF 1,1-DIFLUORO-2-PHENYL-2-PHENYLCYCLOPROPANE AND 1,1-DIFLUORO-3-METHYL-2-PHENYLCYCLOPROPANE [J].

ISOGAI, K ;

NISHIZAWA, N ;

SAITO, T ;

SAKAI, J .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (05) :1555-1556

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