Asymmetric Synthesis of Highly Functionalized Tetrahydrothiophenes by Organocatalytic Domino Reactions

Sven Brandau (1) , Eddy Maerten (1) , Karl Anker Jørgensen (1)

1 Department of Chemistry [Aarhus]

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.

Domaines: Chimie organique; Catalyse

Sven Brandau, Eddy Maerten, Karl Anker Jørgensen. Asymmetric Synthesis of Highly Functionalized Tetrahydrothiophenes by Organocatalytic Domino Reactions. Journal of the American Chemical Society, 2006, 128 (46), pp.14986 - 14991. ⟨10.1021/ja065507+⟩. ⟨hal-03412829⟩