Synthesis of novel oxazaborolidines B-C6F5 and their effectiveness as asymmetric catalysts

Synthesis of novel oxazaborolidines B-C6F5 and their effectiveness as asymmetric catalysts
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DOI:
10.1016/j.jfluchem.2007.07.012
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发表时间:
2007-10
影响因子:
1.9
通讯作者:
T. Korenaga;Fuminao Kobayashi;K. Nomura;Shiho Nagao;T. Sakai
T. Korenaga;Fuminao Kobayashi;K. Nomura;Shiho Nagao;T. Sakai
中科院分区:
化学4区
文献类型:
--
作者:
T. Korenaga;Fuminao Kobayashi;K. Nomura;Shiho Nagao;T. Sakai

文献摘要

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以C6F5B(OMe)2(代替C6F5B(OH)2)和相应的氨基醇为原料,采用改性工艺合成了新型恶唑硼烷b - c6f5,目的是了解c6f5基团在酮类不对称还原中的π -π堆积和吸电子效应。虽然结果不能简单地用预期效应来解释,但b - c6h55和B-C6F5催化剂的对映选择性有显著差异。
Novel oxazaborolidines B-C6F5were synthesized by modified protocol from C6F5B(OMe)2(in place of usual C6F5B(OH)2) and the corresponding amino alcohols, aiming to know the π–π stacking and electron-withdrawing effects of C6F5group in asymmetric reduction of ketones. Although the results were not simply explained by the expected effects, significant difference was observed in the enantioselectivity between the catalysts with B-C6H5and B-C6F5.