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First catalytic enantioselective version of a thia hetero-Diels–Alder reaction with dithioesters

✍ Scribed by Hélène Dentel; Isabelle Chataigner; Fabien Le Cavelier; Mihaela Gulea

Book ID
104098338
Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
285 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

The first example of a catalytic asymmetric thia hetero-Diels-Alder reaction, in which a chiral Lewis acid activates the thiocarbonyl dienophile, is described. The reactions catalyzed by copper(II)-bis(oxazolines) complexes of three dithioesters with simple dienes (such as cyclopentadiene or 2,3-dimethyl-1,3-butadiene) afford optically active dihydrothiopyrans with ees up to 82%. Some aspects of the reaction were investigated by computational means.

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