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- Title
Asymmetric syn‐1,3‐Dioxane Construction via Kinetic Resolution of Secondary Alcohols Using Chiral Phosphoric Acid Catalysts.
- Authors
Matsumoto, Akira; Asano, Keisuke; Matsubara, Seijiro
- Abstract
Herein, we present a novel enantioselective hemiacetalization/intramolecular oxy‐Michael addition cascade for the synthesis of syn‐1,3‐diol frameworks via kinetic resolution of chiral secondary alcohols using chiral phosphoric acid catalysts. By utilizing the recovered optically active starting material, both enantiomers of the corresponding protected 1,3‐diols could be obtained with high optical purities. In addition, the products with a carbonyl group were converted diastereoselectively to longer optically active 1,3‐polyols, which are representative motifs in polyketides. Moreover, the organocatalytic approach presented in this study facilitates a library construction of useful chiral building blocks for the asymmetric synthesis of bioactive compounds.
- Subjects
KINETIC resolution; ACID catalysts; PHOSPHORIC acid; ENANTIOMERIC purity; GLYCOL synthesis; CHIRALITY
- Publication
Asian Journal of Organic Chemistry, 2019, Vol 8, Issue 6, p814
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.201900239