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

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Abstract
Even moderately nucleophilic dienes react with simple aldehydes in the presence of a new CrIII 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.