有机催化蒽酮与β-硝基烯烃的不对称Michael加成反应

doi:10.11944/j.issn.1000-0518.2015.04.140313

摘要/Abstract

摘要：

将金鸡纳生物碱衍生物用于催化蒽酮和β-硝基芳基乙烯的不对称Michael加成反应。考察了溶剂、温度及催化剂用量对反应催化性能的影响。结果表明,最佳条件为5%(摩尔分数)催化剂1b、甲苯为溶剂、0 ℃反应,得到了91%~99%的化学产率和最高达95%ee的对映体选择性。

关键词: 金鸡纳生物碱衍生物, 有机催化, 不对称Michael加成反应, 蒽酮, β-硝基烯烃

Abstract:

Cinchona alkaloid derivatives as organocatalysts were applied in asymmetric Michael addition reaction of anthrone with various trans-β-nitroolefins. Solvent, temperature and catalyst loading were screened. The optimized conditions are using toluene as the solvent with a 5%(molar fraction) loading of catalyst 1b at room temperature. The products are obtained in 91%~99% yield with up to 95%ee.

Key words: Cinchona alkaloid derivative, organocatalysis, asymmetric Michael addition, anthrone, β-nitroolefins

中图分类号:

O621.3

张天一, 年文霞, 金瑛. 有机催化蒽酮与β-硝基烯烃的不对称Michael加成反应[J]. 应用化学, 2015, 32(4): 422-427.

ZHANG Tianyi, NIAN Wenxia, JIN Ying . Organocatalytic Asymmetric Michael Addition of Anthrone with β-Nitroolefins[J]. Chinese Journal of Applied Chemistry, 2015, 32(4): 422-427.

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