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

A new domino autocatalytic reaction leading to polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes
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一种新的多米诺骨牌自催化反应,产生多功能化螺[5.5]十一烷和二螺[4.2.5.2]十五烷

DOI:
10.1039/b822645h
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发表时间:
2009-01-01
影响因子:
3.2
通讯作者:
Shi, Feng
Shi, Feng
中科院分区:
化学3区
文献类型:
--
作者:
Jiang, Bo;Hao, Wen-Juan;Shi, Feng

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本文报道了一种新的亚胺与Meldrum酸的多米诺自催化反应。该反应在酸性条件下成功地合成了一系列多环螺[5.5]十一烷-1,5,9-三酮和双螺[4.2.5.2]十五烷-9,13-二酮衍生物,它们具有显著的非对映选择性,并伴随着亚胺的C=N键断裂和Meldrum酸的分解生成了多达6个新的键,副产物乙酰肼是一种新型的自催化剂。
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.