Recrossing and dynamic matching effects on selectivity in a Diels-Alder reaction.

Recrossing and dynamic matching effects on selectivity in a Diels-Alder reaction.
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DOI:
10.1002/anie.200903293
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发表时间:
2009
影响因子:
16.6
通讯作者:
Singleton, Daniel A.
Singleton, Daniel A.
中科院分区:
化学1区
文献类型:
--
作者:
Wang, Zhihong;Hirschi, Jennifer S.;Singleton, Daniel A.

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丙烯醛与甲基乙烯基酮的杂狄尔斯-阿尔德反应产生的产物来自单一过渡态,轨迹研究准确地预测了选择性。在卡彭特动态匹配思想的延伸中,形成的乘积是由通过过渡态的运动方向决定的。环加成过渡态的重新交叉广泛发生并减少了次要产物的形成。
The products from the hetero-Diels-Alder reaction of acrolein with methyl vinyl ketone arise from a single transition state and trajectory studies accurately predict the selectivity. In an extension of the dynamic matching idea of Carpenter, the product formed is determined by the direction of motion passing through the transition state. Recrossing of the cycloaddition transition state occurs extensively and decreases formation of the minor product.
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