Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Chiral Lewis Acid-Catalyzed Asymmetric Diels-Alder Reactions of (E)-1-Phenylsulfonyl-3-alken-2-ones with Cyclopentadiene
Eiji WadaWen PeiShuji Kanemasa
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1994 Volume 23 Issue 12 Pages 2345-2348

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Abstract

Highly enantio- and endo-selective Diels-Alder reactions of (E)-1-phenylsulfonyl-3-alken-2-ones, a new type of chelating dienophile, with cyclopentadiene are achieved by the aid of a catalytic amount of chiral titanium catalysts. Mode of enantioselectivities depend upon the size of aryl substituents involved in the chiral ligands; dramatic reversal of selectivities is observed.

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© 1994 The Chemical Society of Japan
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