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Synfacts 2010(4): 0476-0476  
DOI: 10.1055/s-0029-1219522
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Benzoheterocycle Synthesis via Diphosphine Catalysis

Contributor(s): Benjamin List, Saihu Liao
V. Sriramurthy, O. Kwon*
University of California, Los Angeles, USA
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Publikationsverlauf

Publikationsdatum:
22. März 2010 (online)

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Significance

The authors reported a method to construct seven different types of ­benzo-fused heterocyles 3 - indolines, dihydro­pyrrolopyridines, benzimidazolines, dihydrobenzo-3,1-oxazines, benzomorpholines, tetrahydroquinolines, and tetrahydroisoquinolines - from simple dinucleophiles 1 and electron-deficient acetylenes 2. Diphenyl­phosphinopropane (DPPP) is an efficient catalyst for this mixed double Michael addition process. In some cases the addition of the AcOH-NaOAc pair can further increase the yields.