A new domino autocatalytic reaction leading to polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes.
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.
College of Chemistry, Chemical Engineering, and Materials Science, Suzhou University, Suzhou, P. R. China.
Bo
B
Jiang
Wen-Juan
WJ
Hao
Jin-Peng
JP
Zhang
Shu-Jiang
SJ
Tu
Feng
F
Shi
D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004146:Dioxanes / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D015394:Molecular Structure
D000473:Alkanes; D004146:Dioxanes; D007097:Imines; C033245:pentadecane; C076489:Meldrum's acid; C022884:undecane