Organic Letters
Organic Letters
5 years ago

Gold(I)-Catalyzed [2 + 2 + 2] Cyclotrimerization of 1,3-Diarylpropargyl Acetals

Gold(I)-Catalyzed [2 + 2 + 2] Cyclotrimerization of 1,3-Diarylpropargyl Acetals
Helgi Freyr Jónsson, Sigvart Evjen, Anne Fiksdahl
A gold-nitrone catalyzed [2 + 2 + 2] cyclotrimerization of 1,3-diarylpropargyl acetals into cyclohexylidene products (up to 74% yield) is reported. The trimerization is proposed to proceed through allenic intermediates via gold-catalyzed 1,3-alkoxy rearrangement. The presence of catalytic amounts of different nitrones, tuning of the Au(I) catalyst activity, was essential for controlled regio-/chemoselective cyclotrimerization. A linear nitrone–O–Au(I)–P coordination mode was shown (X-ray analysis) for a catalytic active phosphane–gold–nitrone complex, representing a group of Au(I) catalysts with specific properties.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00411

DOI: 10.1021/acs.orglett.7b00411

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