Origins of stereoselectivity in Diels-Alder cycloadditions catalyzed by chiral imidazolidinones
Origins of stereoselectivity in Diels-Alder cycloadditions catalyzed by chiral imidazolidinones
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DOI：
10.1021/ja0525859
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发表时间：
2006-03-22
影响因子：
15
通讯作者：
Houk, KN
中科院分区：
文献类型：
--
作者：
Gordillo, R;Houk, KN
利用B3LYP/6-31 G(d)密度泛函理论研究了麦克米伦手性咪唑烷酮有机催化环戊二烯与α、β -不饱和醛和酮的Diels-Alder反应。确定了过渡结构和反应中间体的优选构象。两种相似的手性咪唑烷酮具有明显不同的反应活性和对映选择性。
B3LYP/6-31 G(d) density functional theory has been used to study Diels-Alder reactions of cyclopentadiene with alpha,beta-unsaturated aldehydes and ketones organocatalyzed by MacMillan's chiral imidazolidinones. Preferred conformations of transition structures and reaction intermediates have been located. The dramatically different reactivities and enantioselectivities exhibited by two similar chiral imidazolidinones are rationalized.