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Synfacts 2006(8): 0777-0777  
DOI: 10.1055/s-2006-941980
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2-Phosphonopyrroles

Contributor(s): Victor Snieckus, Bärbel Wittel
K. Moonen, N. Dieltiens, C. V. Stevens*
Ghent University, Belgium
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

A one-pot ring-closing metathesis (RCM) and oxidation sequence of functionalized α-aminoalkenyl phosphates to give 2-phosphono­pyrroles is reported. The starting α,β-unsaturated N-alkylaldimines were readily prepared in moderate yields by regioselective phosphorylation followed by N-benzylation. The RCM-oxidation sequence was performed under second generation Grubbs catalysis. Following tetrachloroquinone oxidation, the products were obtained in 70-84% yields (N-benzyl derivatives) and in 27-39% yields (N-unprotected derivatives).