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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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Article information


Submitted
18 Sep 2006
Accepted
23 Oct 2006
First published
20 Nov 2006

Org. Biomol. Chem., 2007,5, 151-159
Article type
Paper

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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