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

Authors

Alexander G Dossetter, Timothy F Jamison, Eric N Jacobsen

Publication date

1999/8/16

Journal

Angewandte Chemie International Edition

Volume

Issue

Pages

2398-2400

Publisher

WILEY‐VCH Verlag GmbH

Description

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.

Total citations

Cited by 398

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Highly Enantio‐and Diastereoselective Hetero‐Diels–Alder Reactions Catalyzed by New Chiral Tridentate Chromium (iii) Catalysts

AG Dossetter, TF Jamison, EN Jacobsen - Angewandte Chemie International Edition, 1999