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

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

doi:10.1016/j.tetlet.2006.04.091

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

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

Mahidol University

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4753-4757
Number of pages	5
Journal	Tetrahedron Letters
Volume	47
Issue number	27
DOIs	https://doi.org/10.1016/j.tetlet.2006.04.091
Publication status	Published - 3 Jul 2006
Externally published	Yes

Keywords

Aldol-Tishchenko reaction
Samarium dienolate

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10.1016/j.tetlet.2006.04.091

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

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.",

keywords = "Aldol-Tishchenko reaction, Samarium dienolate",

author = "Vichai Reutrakul and Jaray Jaratjaroonphong and Patoomratana Tuchinda and Chutima Kuhakarn and Palangpon Kongsaeree and Samran Prabpai and Manat Pohmakotr",

year = "2006",

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doi = "10.1016/j.tetlet.2006.04.091",

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T1 - Samarium dienolate mediated stereoselective synthesis of anti-1,3-diol monoesters via aldol-Tishchenko reaction

AU - Reutrakul, Vichai

AU - Jaratjaroonphong, Jaray

AU - Tuchinda, Patoomratana

AU - Kuhakarn, Chutima

AU - Kongsaeree, Palangpon

AU - Prabpai, Samran

AU - Pohmakotr, Manat

PY - 2006/7/3

Y1 - 2006/7/3

N2 - 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.

AB - 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.

KW - Aldol-Tishchenko reaction

KW - Samarium dienolate

UR - https://www.scopus.com/pages/publications/33744532073

U2 - 10.1016/j.tetlet.2006.04.091

DO - 10.1016/j.tetlet.2006.04.091

M3 - Article

AN - SCOPUS:33744532073

SN - 0040-4039

VL - 47

SP - 4753

EP - 4757

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 27

ER -

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

Abstract

Keywords

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