Volume 31, Issue 16
Natural Products
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ChemInform Abstract: Axially Chiral Amidinium Ions as Inducers of Enantioselectivity in Diels—Alder Reactions.

Tilmann Schuster

Tilmann Schuster

Inst. Org. Chem., Johann Wolfgang Goethe-Univ., D-60439 Frankfurt/M., Germany

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Markus Bauch

Markus Bauch

Inst. Org. Chem., Johann Wolfgang Goethe-Univ., D-60439 Frankfurt/M., Germany

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Gerd Duerner

Gerd Duerner

Inst. Org. Chem., Johann Wolfgang Goethe-Univ., D-60439 Frankfurt/M., Germany

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Michael W. Goebel

Michael W. Goebel

Inst. Org. Chem., Johann Wolfgang Goethe-Univ., D-60439 Frankfurt/M., Germany

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First published: 09 June 2010

Abstract

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ChemInform Abstract

Diketones of type (II) form hydrogen bonds with lipophilic amidinium ions. Thus, the Diels—Alder reaction of diene (I) with dienophile (II) in the presence of catalytic amounts of chiral amidinium salt provides the steroid skeletons (III) and (IV) with moderate enantioselectivities.

chemical structure image

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