Access to Polyfunctionalized Diquinanes, Hydrindanes, and Decalines via TiCl4 Promoted Michael-Aldol and Baylis-Hillman Reactions

被引：33

作者：

Ressault, Blandine ^{[1
]}

Jaunet, Alexis ^{[1
]}

Geoffroy, Philippe ^{[1
]}

Goudedranche, Sebastien ^{[1
]}

Miesch, Michel ^{[1
]}

机构：

[1] Univ Strasbourg, Inst Chim, UMR UdS CNRS 7177, Lab Chim Organ Synthet, F-67008 Strasbourg, France

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 01期

关键词：

ALPHA; BETA-UNSATURATED KETONES; BETA-ACETYLENIC KETONES; VICINAL DIFUNCTIONALIZATION; ASYMMETRIC CYCLIZATION; STRYKERS REAGENT; ALDEHYDES; ESTERS; HYDROGENATION; CAPNELLENES;

D O I：

10.1021/ol203118t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of 0.5 equiv of TiCl4 to (cyclo)alkanones tethered to alpha,beta-unsaturated ketones afforded polyfunctionalized diquinanes, hydrindanes, and decalines. These products, resulting from a Michael-aldol or a Baylis-Hillman reaction, can be obtained with high or total diastereoselectivity in moderate to high yields. These scaffolds represent interesting building blocks for the synthesis of complex natural products.

引用

页码：366 / 369

页数：4

共 43 条

[1] ADDITIVE AND MEDIUM EFFECTS ON LEWIS ACID-PROMOTED CATIONIC PI-CYCLIZATIONS OF ALKENYLCYCLOPENTANE-1,3-DIONES AND ALKYNYLCYCLOPENTANE-1,3-DIONES [J].