Green chemistry: solvent- and metal-free Prins cyclization. Application to sequential reactions

被引：26

作者：

Clarisse, Damien ^{[1
]}

Pelotier, Beatrice ^{[1
]}

Piva, Olivier ^{[1
]}

Fache, Fabienne ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, ICBMS, Equipe SURCOOF,UMR 5246, F-69622 Villeurbanne, France

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 01期

关键词：

HOMOPROPARGYLIC ALCOHOL; CATALYZED SYNTHESIS; IONIC LIQUIDS; TETRAHYDROPYRANS; STRATEGIES;

D O I：

10.1039/c1cc16501a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Prins cyclization between a homoallylic alcohol and an aldehyde, promoted by trimethylsilyl halide, afforded 4-halo-tetrahydropyrans with good to excellent yields. Thanks to the absence of the solvent and metal, the THP thus obtained have been implicated without purification in several other reactions, in a sequential way, affording in particular new indole derivatives.

引用

页码：157 / 159

页数：3

共 31 条

[1] One single catalyst, Pd(OAc)2, for two sequential very different steps: allylic alcohol oxidation-Heck reaction. Access to functionalised α,β-unsaturated ketones [J].

Batt, Frederic ;

Gozzi, Christel ;

Fache, Fabienne .

CHEMICAL COMMUNICATIONS, 2008, (44) :5830-5832

[2] Synthesis of 1,3-dioxanes catalyzed by TsOH-SiO2 under solvent-free conditions [J].

Borah, Kalyan Jyoti ;

Phukan, Mridula ;

Borah, Ruli .

SYNTHETIC COMMUNICATIONS, 2008, 38 (18) :3082-3087

[3] MECHANISTIC STUDIES ON THE REACTION OF NITROARENES AND NITROSOARENES WITH VINYL GRIGNARD-REAGENTS [J].

BOSCO, M ;

DALPOZZO, R ;

BARTOLI, G ;

PALMIERI, G ;

PETRINI, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (05) :657-663

[4] Stereocontrolled Synthesis of the Highly Functionalized Core Structure of Aurisides by Ring-Closing Metathesis [J].

Bourcet, Emmanuel ;

Fache, Fabienne ;

Piva, Olivier .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (21) :4075-4087

[5] Synthesis of the macrolactone structure of the aurisides [J].

Bourcet, Emmanuel ;

Fache, Fabienne ;

Piva, Olivier .

TETRAHEDRON, 2010, 66 (06) :1319-1326

[6] 5- and 6-exocyclic products, cis-2,3,5-trisubstituted tetrahydrofurans, and cis-2,3,6-trisubstituted tetrahydropyrans via Prins-type cyclization [J].

Chavre, Satish N. ;

Choo, Hyunah ;

Lee, Jae Kyun ;

Pae, Ae Nim ;

Kim, Youseung ;

Cho, Yong Seo .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) :7467-7471

[7] Strategies for the formation of tetrahydropyran rings in the synthesis of natural products [J].

Clarke, Paul A. ;

Santos, Soraia .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (09) :2045-2053

[8] Strategies for the synthesis of tetrahydropyran-containing natural products [J].

Clarke, Paul A. .

TETRAHEDRON, 2011, 67 (27-28) :4959-4959

[9] Enantioselective Synthesis of (-)-Exiguolide by Iterative Stereoselective Dioxinone-Directed Prins Cyclizations [J].

Crane, Erika A. ;

Zabawa, Thomas P. ;

Farmer, Rebecca L. ;

Scheidt, Karl A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) :9112-9115

[10] Total synthesis of indoles from Tricholoma species via Bartoli/heteroaryl radical methodologies [J].

Dobbs, A .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) :638-641

← 1 2 3 4 →