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Title: Samarium dienolate mediated stereoselective synthesis of anti-1,3-diol monoesters via aldol-Tishchenko reaction
Authors: Vichai Reutrakul
Jaray Jaratjaroonphong
Patoomratana Tuchinda
Chutima Kuhakarn
Palangpon Kongsaeree
Samran Prabpai
Manat Pohmakotr
Mahidol University
Keywords: Biochemistry, Genetics and Molecular Biology;Chemistry;Pharmacology, Toxicology and Pharmaceutics
Issue Date: 3-Jul-2006
Citation: Tetrahedron Letters. Vol.47, No.27 (2006), 4753-4757
Abstract: 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. © 2006 Elsevier Ltd. All rights reserved.
ISSN: 00404039
Appears in Collections:Scopus 2006-2010

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