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

Issued Date

2006-07-03

Resource Type

Article

ISSN

00404039

DOI

10.1016/j.tetlet.2006.04.091

Other identifier(s)

2-s2.0-33744532073

Rights

Mahidol University

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SCOPUS

Bibliographic Citation

Tetrahedron Letters. Vol.47, No.27 (2006), 4753-4757

Suggested Citation

Vichai Reutrakul, Jaray Jaratjaroonphong, Patoomratana Tuchinda, Chutima Kuhakarn, Palangpon Kongsaeree, Samran Prabpai, Manat Pohmakotr Samarium dienolate mediated stereoselective synthesis of anti-1,3-diol monoesters via aldol-Tishchenko reaction. Tetrahedron Letters. Vol.47, No.27 (2006), 4753-4757. doi:10.1016/j.tetlet.2006.04.091 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/23008

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Title

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

Author(s)

Vichai Reutrakul
 Jaray Jaratjaroonphong
 Patoomratana Tuchinda
 Chutima Kuhakarn
 Palangpon Kongsaeree
 Samran Prabpai
 Manat Pohmakotr

Other Contributor(s)

Mahidol University

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.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry
 Pharmacology, Toxicology and Pharmaceutics

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URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/23008

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Scopus 2006-2010