Issue 18, 2008

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

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

Supplementary files

Article information

Article type
Paper
Submitted
16 Jun 2008
Accepted
26 Jun 2008
First published
25 Jul 2008

Org. Biomol. Chem., 2008,6, 3366-3370

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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