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. 1999 Aug;38(16):2398-2400.
doi: 10.1002/(sici)1521-3773(19990816)38:16<2398::aid-anie2398>3.0.co;2-e.

Highly Enantio- and Diastereoselective Hetero-Diels-Alder Reactions Catalyzed by New Chiral Tridentate Chromium(III) Catalysts

AG Dossetter  1 , TF Jamison, EN Jacobsen
Affiliations

Highly Enantio- and Diastereoselective Hetero-Diels-Alder Reactions Catalyzed by New Chiral Tridentate Chromium(III) Catalysts

AG Dossetter et al. Angew Chem Int Ed Engl. 1999 Aug.

Abstract

Even moderately nucleophilic dienes react with simple aldehydes in the presence of a new Cr(III) catalyst in a hetero-Diels-Alder reaction [Eq. (1)]. Tetrahydropyranyl products with up to three stereogenic centers are generated in near-perfect diastereoselectivities and with greater than 90 % ee (99 % ee for the example shown). TBAF=tetrabutylammonium fluoride; TBS=tert-butyldimethylsilyl; TES=triethylsilyl.

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