Titanocene(III) Chloride Mediated Stereoselective Synthesis of Trisubstituted Tetrahydrofurans and a Spirolactone by Tandem Radical Reactions

被引：5

作者：

Mukherjee, Shirshendu ^{[1
]}

Roy, Rajdip ^{[1
]}

Roy, Subhas Chandra ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 14期

关键词：

Synthetic methods; C-C coupling; Radicals; Cyclization; Titanium; Spiro compounds; BAYLIS-HILLMAN REACTION; METHYLENE-GAMMA-BUTYROLACTONES; BIOLOGICAL EVALUATION; STRAIGHTFORWARD SYNTHESIS; SESQUITERPENE LACTONES; STRUCTURE REQUIREMENT; CONJUGATE ADDITION; CATALYZED REACTION; HYBRID MOLECULES; EASY ACCESS;

D O I：

10.1002/ejoc.201400097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The titanocene(III) chloride (Cp2TiCl) mediated stereoselective synthesis of highly substituted tetrahydrofurans has been achieved by a reaction that proceeds through a tandem radical cyclization reaction between a Baylis-Hillman adduct and an activated bromo/iodo compound. The reaction of an epoxide with the Baylis-Hillman adduct furnished a spirolactone through a radical cyclization followed by an in situ lactonization. Cp2TiCl was prepared in situ from commercially available Cp2TiCl2 and zinc dust in tetrahydrofuran.

引用

页码：2980 / 2985

页数：6

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