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Stereoselective ozonolysis of TMS-substituted allylic alcohol derivatives and synthesis of 14R,15S- and 14S,15S-diHETE

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Abstract

Ozonolysis of TMS-substituted olefins produces α-carbonyl TMS peroxides without cleavage of the C[double bond, length as m-dash]C bond. Herein, stereochemistry in the ozonolysis was studied using silyl derivatives of (E)- and (Z)-(1-TMS)alk-1-en-3-ols. The (E)-isomers afforded the anti-3-siloxy-2-(TMS-oxy)aldehydes as the major stereoisomer (anti/syn = 3–9 : 1) after reductive work-up with Ph3P. In contrast, Z-olefins selectively gave the syn isomers with syn/anti ratios of 4–19 : 1. Facial selection was speculated based on the Cieplak effect. This ozonolysis was successfully applied for the synthesis of 14R,15S- and 14S,15S-diHETEs (anti and syn isomers, respectively) in enantioenriched forms.

Graphical abstract: Stereoselective ozonolysis of TMS-substituted allylic alcohol derivatives and synthesis of 14R,15S- and 14S,15S-diHETE

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Publication details

The article was received on 29 Aug 2018, accepted on 24 Sep 2018 and first published on 24 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB02116C
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Stereoselective ozonolysis of TMS-substituted allylic alcohol derivatives and synthesis of 14R,15S- and 14S,15S-diHETE

    S. Saito, T. Yamazaki and Y. Kobayashi, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02116C

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