Chiral phosphoric acid catalyzed highly enantioselective desymmetrization of 2-substituted and 2,2-disubstituted 1,3-diols via oxidative cleavage of benzylidene acetals.

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ID: 238226
2014
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Abstract
A highly enantioselective catalytic protocol for the desymmetrization of a wide variety of 2-substituted and 2,2-disubstituted 1,3-diols is reported. This reaction proceeds through the formation of an "ortho ester" intermediate via oxidation of 1,3-diol benzylidene acetal by dimethyldioxirane (DMDO) and the subsequent proton transfer catalyzed by chiral phosphoric acid (CPA). The mechanism and origins of enantioselectivity of this reaction are identified using DFT calculations. The oxidation by DMDO is rate-determining, and the phosphoric acid significantly accelerates the proton transfer; the attractive interactions between the benzylidene part of the substrate and the 2,4,6-triisopropyl group of CPA are the key to high enantioselectivity.
Reference Key
meng2014chiraljournal Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Meng, Shan-Shui;Liang, Yong;Cao, Kou-Sen;Zou, Lufeng;Lin, Xing-Bang;Yang, Hui;Houk, K N;Zheng, Wen-Hua;
Journal Journal of the American Chemical Society
Year 2014
DOI
10.1021/ja507332x
URL
Keywords
photochemistry reactivity polyolefins diels–alder reactions bromination epoxidation hydrogenation

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