Switching of product's chirality in diastereodifferentiating [2+2] photocycloaddition of (E)- versus (Z)-stilbene to chiral fumarate upon direct and charge-transfer-band excitation.
Switching of product's chirality in diastereodifferentiating [2+2] photocycloaddition of (E)- versus (Z)-stilbene to chiral fumarate upon direct and charge-transfer-band excitation.
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DOI：
10.1021/ol060468s
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发表时间：
2006-04
期刊：
影响因子：
5.2
通讯作者：
H. Saito;Tadashi Mori;T. Wada;Y. Inoue
中科院分区：
文献类型：
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作者：
H. Saito;Tadashi Mori;T. Wada;Y. Inoue
[反应：见正文]通过二苯乙烯的直接激发和电荷转移(CT)络合物的选择性激发，(E)-和(Z)-二苯乙烯在不同温度下进行了[2+2]光环加成富马酸二((R)-1-甲丙基)的反应。在两种激发方式下，二苯乙烯的几何异构体提供了与木曲克辛相反的非对映异构体，随着长时间的照射，产物的非对映选择性显著降低。
[reaction: see text] Diastereodifferentiating [2+2] photocycloadditions of (E)- and (Z)-stilbenes to bis((R)-1-methylpropyl) fumarate were performed through the direct excitation of stilbenes and the selective excitation of the charge-transfer (CT) complex at various temperatures. The geometrical isomers of stilbene afforded the opposite diastereomers of mu-truxinate in both excitation modes, with a dramatic decrease in the product's diastereoselectivity upon prolonged irradiations.