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Issue 18, 2008
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Regioselective synthesis of functionalized 3,5-diketoesters and 2,4-diketosulfones by uncatalyzed condensation of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadienes with α,β-unsaturated acid chlorides and sulfonyl chlorides

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Abstract

The reaction of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadienes with α,β-unsaturated and functionalized acid chlorides afforded a variety of 3,5-diketoesters which are not readily available by other methods. The reaction of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with sulfonyl chlorides allows a direct synthesis of 2,4-diketosulfones.

Graphical abstract: Regioselective synthesis of functionalized 3,5-diketoesters and 2,4-diketosulfones by uncatalyzed condensation of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadienes with α,β-unsaturated acid chlorides and sulfonyl chlorides

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Article information


Submitted
16 Jun 2008
Accepted
26 Jun 2008
First published
25 Jul 2008

Org. Biomol. Chem., 2008,6, 3366-3370
Article type
Paper

Regioselective synthesis of functionalized 3,5-diketoesters and 2,4-diketosulfones by uncatalyzed condensation of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadienes with α,β-unsaturated acid chlorides and sulfonyl chlorides

T. Rahn, T. H. T. Dang, A. Spannenberg, C. Fischer and P. Langer, Org. Biomol. Chem., 2008, 6, 3366
DOI: 10.1039/B810151E

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