Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions.
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.
Brandau
Sven
S
Danish National Research Foundation, Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark.
Maerten
Eddy
E
Jørgensen
Karl Anker
KA
D002384:Catalysis; D020134:Catalytic Domain; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
D013876:Thiophenes; C121030:tetrahydrothiophene