Effect of Conformational Control of Chiral Oxazaborolidine by π—π Stacking Interaction of a Pentafluorophenyl Group Toward Asymmetric Borane Reduction.
Effect of Conformational Control of Chiral Oxazaborolidine by π—π Stacking Interaction of a Pentafluorophenyl Group Toward Asymmetric Borane Reduction.
复制标题
五氟苯基的π-π堆积相互作用对手性恶唑硼烷的构象控制对不对称硼烷还原的影响。
DOI：
10.1002/chin.200735030
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发表时间：
2007
期刊：
影响因子：
--
通讯作者：
T. Sakai
中科院分区：
文献类型：
--
作者：
T. Korenaga;K. Kadowaki;T. Sakai
五氟苯基可以通过与苯基的分子内π-π堆积相互作用在恶唑硼烷催化的不对称硼烷还原中充当立体控制基团。通过计算和~ 1HNMR研究证实了含五氟苯基的恶唑硼烷分子内存在π-π相互作用。相互作用对苯乙酮不对称还原反应的对映选择性有影响，但影响程度较小。
A pentafluorophenyl group can act as a stereo-controlling group in oxazaborolidine-catalyzed asymmetric borane reduction through intramolecular π–π stacking interaction with a phenyl group. The intramolecular π–π interaction in oxazaborolidine bearing pentafluorophenyl group is confirmed by calculations and1H NMR study. The interaction affects the enantioselectivity of the asymmetric reduction of acetophenone while the extent is small.