Organic & Biomolecular Chemistry 2009-05-21

A new domino autocatalytic reaction leading to polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes.

Bo Jiang, Wen-Juan Hao, Jin-Peng Zhang, Shu-Jiang Tu, Feng Shi

Index: Org. Biomol. Chem. 7(10) , 2195-201, (2009)

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Abstract

A new domino autocatalytic reaction of imines with Meldrum's acid was described. In this reaction, a series of polycyclic spiro[5.5]undecane-1,5,9-trione and dispiro[4.2.5.2]pentadecane-9,13-dione derivatives, with remarkable diastereoselectivity, were successfully synthesized in acidic condition, and up to six new bonds were formed accompanied by the C=N bond cleavage of the imines and the decomposition of Meldrum's acid, with by-product of acetohydrazide as a novel autocatalyst.