Reversible-irreversible approach to Schiff base macrocycles: Access to isomeric macrocycles with multiple salphen pockets

Reversible-irreversible approach to Schiff base macrocycles: Access to isomeric macrocycles with multiple salphen pockets
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DOI:
10.1021/ol8001317
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发表时间:
2008-03-20
期刊:
影响因子:
5.2
通讯作者:
MacLachlan, Mark J.
MacLachlan, Mark J.
中科院分区:
化学1区
文献类型:
--
作者:
Frischmann, Peter D.;Jiang, Jian;MacLachlan, Mark J.

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我们开发了利用醛亚胺和酮亚胺的不同汇率形成新的无金属席夫碱大环化合物家族的方法。更牢固的酮亚胺键在用于醛亚胺键形成的较温和条件下是动力学惰性的。特别是,该路线能够获得第一个具有四个不对称 N2O2 salphen 样口袋的共轭大环化合物。
We have developed methodology for the formation of a new family of metal-free Schiff base macrocycles utilizing the differential exchange rates of aldimines and ketimines. The more robust ketimine bond is kinetically inert under the milder conditions used for aldimine bond formation. In particular, this route enables access to the first conjugated macrocycles with four unsymmetrical N2O2 salphen-like pockets.