Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions

被引：230
|
作者：
Brandau, Sven [1 ]
Maerten, Eddy [1 ]
Jorgensen, Karl Anker [1 ]
机构：
[1] Aarhus Univ, Dept Chem, Danish Natl Res Fdn, Ctr Catalysis, DK-8000 Aarhus C, Denmark
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 46期
关键词：
D O I：
10.1021/ja065507+
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A simple approach for the formation of optically active highly functionalized tetrahydrothiophenes, which might find important use in biochemistry, pharmaceutical science, and nanoscience is presented. Development of new organocatalytic Michael-aldol domino reactions is outlined, and with the appropriate choice of additives it is possible to control the regioselectivity of these domino reactions, yielding diastereomerically pure ( tetrahydrothiophen-2-yl) phenyl methanones or tetrahydrothiophene carbaldehydes in good yields and with excellent enantioselectivities up to 96% ee. The stereochemical outcome of these reactions is investigated, and the mechanism of these organocatalytic domino processes is presented.
引用
收藏
页码：14986 / 14991
页数：6
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