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Asymmetric syn ‐1,3‐Dioxane Construction via Kinetic Resolution of Secondary Alcohols Using Chiral Phosphoric Acid Catalysts
Author(s) -
Matsumoto Akira,
Asano Keisuke,
Matsubara Seijiro
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900239
Subject(s) - kinetic resolution , chemistry , enantioselective synthesis , intramolecular force , phosphoric acid , optically active , enantiomer , catalysis , organocatalysis , combinatorial chemistry , diol , organic chemistry , enantiomeric excess
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.