Efficiency of Acid- and Mercury-Catalyzed Cyclization Reactions in the Synthesis of Tetrahydrofurans from Allylsilyl Alcohols

被引：13

作者：

Pulido, Francisco J. ^{[1
]}

Barbero, Asuncion ^{[1
]}

Val, Patricia ^{[1
]}

Diez, Alberto ^{[1
]}

Gonzalez-Ortega, Alfonso ^{[1
]}

机构：

[1] Univ Valladolid, Dept Organ Chem, E-47011 Valladolid, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 27期

关键词：

Synthetic methods; Cyclization; Allenes; Allylic compounds; Oxygen heterocycles; Mercury; SILICON-DIRECTED CYCLIZATION; STEREOSELECTIVE-SYNTHESIS; VINYLSILANES BEARING; ALLENE; SCOPE; CYCLOPROPANATION; CYCLOPENTANE; INDUCTION; STRATEGY; OXO;

D O I：

10.1002/ejoc.201200666

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The scope of the acid-catalyzed and mercury-catalyzed cyclization reactions of allylsilyl alcohols is described. This methodology has been found to be an efficient approach to the synthesis of highly substituted tetrahydrofurans. The stereoselectivity of the cyclization is dependent both on the substitution of the starting alcohol and on the catalyst. A plausible mechanism has been proposed that is consistent with the results.

引用

页码：5350 / 5356

页数：7

共 29 条

[1] Lignans as food constituents with estrogen and antiestrogen activity [J].

Aehle, Elke ;

Mueller, Ulrike ;

Eklund, Patrik C. ;

Willfor, Stefan M. ;

Sippl, Wolfgang ;

Draeger, Birgit .

PHYTOCHEMISTRY, 2011, 72 (18) :2396-2405

[2]

Akiyama T, 1998, SYNLETT, P1150

[3] 1,3-asymmetric induction in electrophilic addition onto homoallylsilanes. An approach towards the total synthesis of (+/-)-kumausyne. [J].

Andrey, O ;

Glanzmann, C ;

Landais, Y ;

ParraRapado, L .

TETRAHEDRON, 1997, 53 (08) :2835-2854

[4] Silylcuprates from allene and their reaction with α,β-unsaturated nitriles and imines.: Synthesis of silylated oxo compounds leading to cyclopentane and cycloheptane ring formation [J].

Barbero, A ;

Blanco, Y ;

Pulido, FJ .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :6876-6883

[5] Spiro-cyclopropanation from oxoallylsilanes [J].

Barbero, A ;

Castreño, P ;

Pulido, FJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) :8022-8023

[6] Allylsilanes and vinylsilanes from silylcupration of carbon-carbon multiple bonds: Scope and synthetic applications [J].

Barbero, A ;

Pulido, FJ .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (10) :817-825

[7] Allene:: As small in size as versatile in synthesis.: A general scope of its usefulness as a C3-synthon for carbocyclic annulations [J].

Barbero, A ;

Pulido, FJ .

SYNTHESIS-STUTTGART, 2004, (05) :779-785

[8] Acid-catalyzed cyclization of epoxyallylsilanes.: An unusual rearrangement cyclization process [J].

Barbero, A ;

Castreño, P ;

Pulido, FJ .

ORGANIC LETTERS, 2003, 5 (22) :4045-4048

[9] Functionalised allylsilanes from silylcopper reagents and allene.: A useful strategy for cyclopentane annulations [J].

Barbero, A ;

García, C ;

Pulido, FJ .

TETRAHEDRON, 2000, 56 (18) :2739-2751

[10]

Barbero A., 2001, CHEM COMMUN, V66, P7723

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