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Issue 1, 2007
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Ti-direct, powerful, stereoselective aldol-type additions of esters and thioesters to carbonyl compounds: application to the synthesis and evaluation of lactone analogs of jasmone perfumes

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Abstract

An efficient TiCl4–Et3N or Bu3N-promoted aldol-type addition of phenyl and thiophenyl esters or thioaryl esters with aldehydes and ketones was performed (total 46 examples). The present method is advantageous from atom-economical and cost-effective viewpoints; good to excellent yields, moderate to good syn-selectivity, substrate variations, reagent availability, and simple procedures. Utilizing the present reaction as the key step, an efficient short synthesis of three lactone [2(5H)-furanone] analogs of jasmine perfumes was performed. Among them, the lactone analog of cis-jasmone had a unique perfume property (tabac).

Graphical abstract: Ti-direct, powerful, stereoselective aldol-type additions of esters and thioesters to carbonyl compounds: application to the synthesis and evaluation of lactone analogs of jasmone perfumes

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Publication details

The article was received on 18 Sep 2006, accepted on 23 Oct 2006 and first published on 20 Nov 2006


Article type: Paper
DOI: 10.1039/B613544G
Org. Biomol. Chem., 2007,5, 151-159

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    Ti-direct, powerful, stereoselective aldol-type additions of esters and thioesters to carbonyl compounds: application to the synthesis and evaluation of lactone analogs of jasmone perfumes

    R. Nagase, N. Matsumoto, K. Hosomi, T. Higashi, S. Funakoshi, T. Misaki and Y. Tanabe, Org. Biomol. Chem., 2007, 5, 151
    DOI: 10.1039/B613544G

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