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. 2015 Jul 6;54(28):8241-4.
doi: 10.1002/anie.201502505. Epub 2015 Jun 1.

Rhodium-Catalyzed [3+2+2] and [2+2+2] Cycloadditions of Two Alkynes with Cyclopropylideneacetamides

Tomoka Yoshida  1 , Yuki Tajima  1 , Masayuki Kobayashi  1 , Koji Masutomi  2 , Keiichi Noguchi  3 , Ken Tanaka  4   5   6
Affiliations

Rhodium-Catalyzed [3+2+2] and [2+2+2] Cycloadditions of Two Alkynes with Cyclopropylideneacetamides

Tomoka Yoshida et al. Angew Chem Int Ed Engl. .

Abstract

It has been established that a cationic rhodium(I)/H8 -binap complex catalyzes the [3+2+2] cycloaddition of 1,6-diynes with cyclopropylideneacetamides to produce cycloheptadiene derivatives through cleavage of cyclopropane rings. In contrast, a cationic rhodium(I)/(S)-binap complex catalyzes the enantioselective [2+2+2] cycloaddition of terminal alkynes, acetylenedicarboxylates, and cyclopropylideneacetamides to produce spiro-cyclohexadiene derivatives which retain the cyclopropane rings.

Keywords: asymmetric catalysis; cycloaddition; heterocycles; rhodium; synthetic methods.

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