Asymmetric Synthesis of Highly Functionalized Tetrahydrothiophenes by Organocatalytic Domino Reactions | Zendy

Sven Brandau | Zendy; Eddy Maerten | Zendy; Karl Anker Jørgensen | Zendy

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Asymmetric Synthesis of Highly Functionalized Tetrahydrothiophenes by Organocatalytic Domino Reactions

Author(s) -

Sven Brandau,

Eddy Maerten,

Karl Anker Jørgensen

Publication year - 2006

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja065507+

Subject(s) - chemistry , domino , tetrahydrothiophene , organocatalysis , aldol reaction , regioselectivity , combinatorial chemistry , cascade reaction , catalysis , organic chemistry , enantioselective synthesis

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.

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