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.
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收藏
页码：366 / 369
页数：4
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