Stereochemical control of skeletal diversity.
Stereochemical control of skeletal diversity.
复制标题
DOI：
10.1021/ol035773h
复制
发表时间：
2003-10
期刊：
影响因子：
5.2
通讯作者：
Jason K. Sello;P. Andreana;Daesung Lee;S. Schreiber
中科院分区：
文献类型：
--
作者：
Jason K. Sello;P. Andreana;Daesung Lee;S. Schreiber
[反应：见原文]。具有预先编码骨架信息（sigma-elements）的附属物的底物可以通过一组共同的反应条件转化为具有不同骨架的产物。依次使用Ugi 4CC-IMDA反应，然后是手性氨基醇附属物（sigma-element）的烯丙基化、水解和酰化，得到ROM/RCM或RCM反应的底物。西格玛元素的立体化学，而不是它的构成控制着所选择的途径的结果。这项工作说明了将立体化学控制与骨骼多样性的挑战性问题联系起来的潜力。
[reaction: see text]. Substrates having appendages that pre-encode skeletal information (sigma-elements) can be converted into products having distinct skeletons using a common set of reaction conditions. The sequential use of the Ugi 4CC-IMDA reaction, followed by allylation, hydrolysis, and acylation of a chiral amino alcohol appendage (sigma-element), leads to substrates for a ROM/RCM or RCM reaction. The stereochemistry of the sigma-element and not its constitution controls the outcome of the pathway selected. This work illustrates the potential of linking stereochemical control to the challenging problem of skeletal diversity.