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
收藏
页码：2980 / 2985
页数：6
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