Samarium dienolate mediated stereoselective synthesis of anti-1,3-diol monoesters via aldol-Tishchenko reaction

The reaction of an ( E)-samarium dienolate, generated by the regioselective reductive cleavage of a phenylsulfonyl activated cyclopropyl ketone with samarium(II) iodide, with aliphatic and aromatic aldehydes gives the 2-substituted anti-1,3-diol monoester derivatives, stereoselectively, in good to e...

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Bibliographic Details
Published in:Tetrahedron letters 2006-07, Vol.47 (27), p.4753-4757
Main Authors: Reutrakul, Vichai, Jaratjaroonphong, Jaray, Tuchinda, Patoomratana, Kuhakarn, Chutima, Kongsaeree, Palangpon, Prabpai, Samran, Pohmakotr, Manat
Format: Article
Language:English
Subjects:
Aldol-Tishchenko reaction
Samarium dienolate
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Summary:The reaction of an ( E)-samarium dienolate, generated by the regioselective reductive cleavage of a phenylsulfonyl activated cyclopropyl ketone with samarium(II) iodide, with aliphatic and aromatic aldehydes gives the 2-substituted anti-1,3-diol monoester derivatives, stereoselectively, in good to excellent yields. The results represent the first report of a dienolate in the aldol-Tishchenko reaction and also provide an optically active polyol with ( R)-glyceraldehyde.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.04.091