Conformational effects in diastereoselective aryne Diels-Alder reactions: synthesis of benzo-fused [2.2.1] heterobicycles.
Conformational effects in diastereoselective aryne Diels-Alder reactions: synthesis of benzo-fused [2.2.1] heterobicycles.
复制标题
DOI：
10.1021/ol9019869
复制
发表时间：
2009-09
期刊：
影响因子：
5.2
通讯作者：
R. Webster;M. Lautens
中科院分区：
文献类型：
--
作者：
R. Webster;M. Lautens
结果表明，芳炔与取代呋喃之间的Diels-Alder反应的非对映选择性对取代反应非常敏感，从而影响了反应构象。通过改变基团在二烯偶体上的位置，可以获得优异的化学产率和高立体选择性。这种方法提供了快速和方便的途径获得对映体纯双环支架，这是其他方法难以制备的。
It was found that the diastereoselectivity of the Diels-Alder reaction between arynes and substituted furans is highly sensitive to substitution, which affects the reactive conformation. By varying the location of the groups on the diene partner, it is possible to obtain both excellent chemical yields and high stereoselectivity. This methodology offers rapid and convenient access to enantiomerically pure bicyclic scaffolds which are difficult to prepare by other means.