Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091 China.
Chem Asian J. 2011 Jan 3;6(1):220-5. doi: 10.1002/asia.201000561.
The first catalytic asymmetric conjugate addition of 1,3-dicarbonyl compounds to nitroenynes catalyzed by cinchona alkaloid-based thiourea organocatalysts has been developed. The 1,4-addition adducts were obtained solely, in moderate to good yields (up to 93%) with good enantioselectivities (up to 99% ee). This protocol affords a conceptually different entry to the precursors of pharmaceutically important chiral β-alkynyl acid derivatives and synthetically useful chiral nitroalkynes. Notably, the protocol worked well with both aryl- and alkyl-substituted alkynyl substrates.
手性硫脲型金鸡纳生物碱催化的 1,3-二羰基化合物与硝基烯炔的首例不对称共轭加成反应已被开发。该反应以中等至优秀的收率（高达 93%）和良好的对映选择性（高达 99%ee）得到了 1,4-加成产物。该方法为具有重要药用价值的手性β-炔基酸衍生物和合成有用的手性硝基炔前体提供了一种不同的概念途径。值得注意的是，该方法在手性硫脲型金鸡纳生物碱催化的 1,3-二羰基化合物与硝基烯炔的首例不对称共轭加成反应已被开发。该反应以中等至优秀的收率（高达 93%）和良好的对映选择性（高达 99%ee）得到了 1,4-加成产物。该方法为具有重要药用价值的手性β-炔基酸衍生物和合成有用的手性硝基炔前体提供了一种不同的概念途径。值得注意的是，该方法在芳基和烷基取代的炔基底物中都能很好地发挥作用。
