有机小分子催化MBH碳酸酯的不对称烯丙基硅醚化反应研究
发布时间：2018-10-30 15:20
【摘要】：烯丙基化合物和各种亲核试剂(例如C、N、O、P、S、B等)的不对称亲核取代反应是构建碳-碳、碳-杂键的一种常见方法,该方法在有机合成领域有着重要的应用。烯丙基硅化合物是一类重要的有机合成中间体,在半萜类天然产物、药物以及一些复杂结构的环化合物的构建中都有着重要的应用。不对称烯丙基醚化反应无论是在金属催化还是小分子催化方面都得到了国内外化学研究者的广泛关注。相比之下,含硅的亲核试剂(如硅烷和硅醇)在不对称烯丙基取代反应中研究较少。目前,已有三例文章报道不对称烯丙基硅醚化反应,且均在金属催化剂条件下进行。由于过渡金属催化剂的价格昂贵,反应条件苛刻等原因,我们选用反应条件温和,稳定性强,对环境友好的手性金鸡纳碱作催化剂,对较难控制区域选择性的MBH碳酸酯和硅醇的不对称的烯丙基硅醚化反应进行研究。首先,用Ph3SiH作亲核试剂和MBH碳酸酯反应,目标产物结构经过单晶衍射实验确定,意外的发现三苯基硅氧基取代的MBH碳酸酯产物的生成。通过一系列的控制实验,发现Ph3SiH在反应过程中生成了Ph3SiOH。然后,用Ph3SiOH作亲核试剂,对MBH碳酸酯的不对称烯丙基硅醚化反应从催化剂结构、碱的种类、反应底物的比例、溶剂、温度等方面进行了细致的筛选。当催化剂(DHQD)2PYR用量为10 mol%,iPr2EtN(1.0 equiv)作碱,溶剂为甲基叔丁基醚(MTBE)在90 oC下反应12 h,烯丙基硅醚化合物能够得到91%的产率,90%的对映选择性和大于20:1的区域选择性。在优化的条件下,一系列的芳环、杂环、脂肪族MBH碳酸酯(25个化合物)能够和三苯基硅醇得到中等到高的收率(up to 98%),优异的区域选择性(20:1)以及好的对映选择性(up to 92%ee)。当Me2PhSiOH作亲核试剂时,反应也能得到60%的收率和87%的对映选择性。随后对产物进行了适当的衍生。本文的研究工作拓展了有机小分子催化剂在不对称烯丙基硅醚化反应中的应用,三苯基硅醇用作水的替代物不仅能够得到手性醇类的化合物,而且还能得到一系列含硅的手性化合物。文章中新合成的没有文献表征过的化合物都进行了1H NMR,13C NMR,HRMS表征,结构完全正确。部分化合物通过培养单晶进行单晶衍射实验确定化合物结构和手性化合物的绝对构型。
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【学位授予单位】：河南师范大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.251
本文编号：2300376
[Abstract]:% E7%83%AF%E4%B8%99%E5%9F%BA%E5%8C%96%E5%90%88%E7%89%A9%E5%92%8C%E5%90%84%E7%A7%8D%E4%BA%B2%E6%A0%B8%E8%AF % 95%E5%89%82%28%E4%BE%8B%E5%A6%82C%2CN%2CO%2CP%2CS%2CB%E7%AD%89%29%E7%9A%84%E4%B8%8D%E5%AF%B9%E7%A7%B0%E4%BA%B2 % E6A0A0B8B _ 5B _ 5B _ 5B _ 5B _ 5B _ 5B _ 5B _ 5B _ 5B _ 5B _ 8B _ 5B _ 5B _ 5B _ 5B _ 5B _ 5B _ 5B _ 8B _ 8B _ 5B _ 5B _ 5b _ 5b _ 5b _ 5b _ 5b _ 5b _ 5b _ 5b _ 5b _ 5b _ 5b _ 5B _ 5B _ 5b _ 5B _ 5B _ 5B _ 5B _ 5B _ 5B _ 5B _ 5B _ 5B _ 5B _ 5B % E6%9D%82%E9%94%AE%E7%9A%84%E4%B8%80%E7%A7%8D%E5%B8%E8%A7%81%E6%96%B9%E6%B3%95%2C%E8%AF%A5%E6%96%B9%E6 % B3%95%E5%9C%A8%E6%9C%89%E6%9C%BA%E5%90%88%E6%88%90%E9%A2%86%E5%9F%9F%E6%9C%89%E7%9D%80%E9%87%8D%E8%A6%81 % E79A8A8A8.8. the side of E79A89F899FBAE799E599E599E599E599E599E599E599E599E599E599E599E599E599E599E599E599E599E599E599E599E590888E73AF8A88A5908885 and the side of E73B8A8A5908885, including E73B8A8A59088I, including the side of E7 B880E78DE8D8DE8D8D8D8D8D8D8D8D8D8DE8D8D8D8D8DE8D8D8D8D8D8D8D8DE8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8DE8D8D8D8D8D8D8D8D8DE8D8D 2CE58C9C9A8D8D8D8A8A8A8A8A8D8D8A8A8A8D8D8A8A8A8A8A8A8D8D8A8A8A8A8D8D8D8A8A8A8A8A88D8D8A8D8A8A8A88D8A8D8A8A8D8A8A8A8A8A9A8A9A9A9A8888D8D8D8A8A8A8A8D8A8A8A8A8 E58F8F8A8A9A, E58F8F8A8A, E58F8F8A8A8E88F8A8A8A84E78D8D8D8A84E784 E78D88D8D88E8B, including E5A88D8D8E8A8E78E784 E78D88D8D8E8A8B, including E5A88D8D8E8B and E88A8D8A8E8A8A8E88E8E88E88E8 A9 E79A8, including A9, E790, and A9, E7, 9A9, and A9, E7, 7, 9, and 8, the right side, right, right. 94%A8.%E4%B8%8D%E5%AF%B9%E7%A7%B0%E7%83%AF%E4%B8%99%E5%9F%BA%E9%86%9A%E5%8C%96%E5%8F%8D%E5%BA%94%E6%97%A0 % E8%AE%BA%E6%98%AF%E5%9C%A8%E9%87%91%E5%B1%9E%E5%82%AC%E5%8C%96%E8%BF%98%E6%98%AF%E5%B0%8F%E5%88%86%E5%AD % 90%E5%82%AC%E5%8C%96%E6%96%B9%E9%9D%A2%E9%83%BD%E5%BE%97%E5%88%B0%E4%BA%86%E5%9B%BD%E5%86%85%E5%A4%96%E5 8C8C8C9A96E58A8C9A9B 9B584 E6885 E7B3A880885 E7B3A88088E7B6B6B6A7B6A7B6A7B6A7B7A7A7B7A7A7B7B7B8B8A8A8A8AF% and E79B8B8E6AF% and E79B8B8B8E6AF% should be included in the center of the unit, including E79B8B8E6AF%. 94E4B9B9C8C8A8A8A8A8A88A88A88B9B9B9B9B9B9B9B9B9B9B98B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B9B98B9B9B98B9B9B9B9 85E73B73B, 82CE7A, 82C7A, 82C7A, 85E73B, 83C7A, 85E73B, 83C7A, 82C7A, 85E73B, 82C7A, 82C7A, 82C7A, 82C78C, 82C7A, 82C7A, 82C78C, 82C7A, 82C7A, 82C7A, 82C7A, 82C7A, 82C7A, 82CE77A, E5%8F%96%E4%BB%A3%E5%8F%8D%E5%BA%94%E4%B8%AD%E7%A0%94%E7%A9%B6%E8%BE%83%E5%B0%91.%E7%9B%AE%E5%89%8D%2C%E5 % B7%B2%E6%9C%89%E4%B8%89%E4%BE%8B%E6%96%87%E7%AB%A0%E6%8A%A5%E9%81%93%E4%B8%8D%E5%AF%B9%E7%A7%B0%E7%83%AF % E4%B8%99%E5%9F%BA%E7%A1%85%E9%86%9A%E5%8C%96%E5%8F%8D%E5%BA%94%2C%E4%B8%94%E5%9D%87%E5%9C%A8%E9%87%91%E5 % B19E9E9E8C968E8C968D8B8B8B8B8B8B8B8B8B88B8B8B8B88B8B882E59B 8C96B and E8E8B9B 8B8B9B1B8B8B 8B8B 8B 8B 8B 8b 8B 8B 8B 8I have the right side of the battery, including the head of the bank, the head of the bank. 87E6B8A1, E9991, E51and E8B52B52B52B52B52B52B52B52B52B52B52B52B52B52B52B52B52B52B52C52C52C52C52C52C52C52C52C52C2C52C2C2C2C2C52C2C2C2C2C2B4B4B4B4B4B52C22C2C2B52C2C2 E58F8F8D8D9D1, including E58F8F8D9D1, including E58F8F8F8E58889E5888E58E58E588B8B8B8B8B9B8B8B8D9D1, including E4BBA1and E4BBAC8ACE9%, including E4BBACE9%. 80899E789E78F8D8DE5, including the following: he was right, right. BA%2C%E5%AF%B9%E7%8E%AF%E5%A2%83%E5%8F%8B%E5%A5%BD%E7%9A%84%E6%89%8B%E6%80%A7%E9%87%91%E9%B8%A1%E7%BA%B3% E7A2B1, E582B1, E582B1B1, E58A9C1B1, E58A9B1B1, and E58A9C9B1, E58C9B1, E588C882, and E588C88C88C58C58C58C58C58C58C58C58C58C58C88E58B5 9F9F9F9F9F9E98F98F98F98F98F9F98F98F98F98F98F98F98F98F98F98E98E98E98E98A98A98A98A98A98A98E7E7E7E98E9808c8E7E7E78A98E9E98088A98A98A98E98E98A88E78A98A988A98A98 E4B88D8D8D8D8D8D8D8D8D8D8D8D8D8D8D88D88D8A78D88D88D88A88D88D88A78A88D88D78A78A88D78A88D78A88D78A78A88A8A88A8A88A88A88A788A88A88A88A888A88A88A88A88A88A88A8 94%E8%BF%9B%E8%A1%8C%E7%A0%94%E7%A9%B6.%E9%A6%96%E5%85%88%2C%E7%94%A8Ph3SiH%E4%BD%9C%E4%BA%B2%E6%A0%B8%E8%AF%95 % E5%89%82%E5%92%8CMBH%E7%A2%B3%E9%85%B8%E9%85%AF%E5%8F%8D%E5%BA%94%2C%E7%9B%AE%E6%A0%87%E4%BA%A7%E7%89%A9%E7 % BB%93%E6%9E%84%E7%BB%8F%E8%BF%87%E5%8D%95%E6%99%B6%E8%A1%8D%E5%B0%84%E5%AE%9E%E9%AA%8C%E7%A1%AE%E5%AE%9A % 2C%E6%84%8F%E5%A4%96%E7%9A%84%E5%8F%91%E7%8E%B0%E4%B8%89%E8%8B%AF%E5%9F%BA%E7%A1%85%E6%B0%A7%E5%9F%BA%E5 % 8FF 8F 8F 8F 8B / h 8F 8F 8F 985 E789A789 E9889 E9885 E7885 E7888A788E78E788A789A789A789A789A789A789A788E78888E7885888888888A788A789A789A789A788E7 9AE8E8BF88BF880E7B3, including the side of E78E8E08SiH%, E78E8E8E8E88E88E88E88E88E88E888B88B3F91E78E8E8E8E8E8E8E8E8E8E8E8E8E88E88B3F91E78E8E0B0F91E78E8E8E8E88B8B3F91E78E0B0F91E78E0H% E5%9C%A8%E5%8F%8D%E5%BA%94%E8%BF%87%E7%A8%8B%E4%B8%AD%E7%94%9F%E6%88%90%E4%BA%86Ph3SiOH.%E7%84%B6%E5%90%8E%2C%E7 % 94%A8Ph3SiOH%E4%BD%9C%E4%BA%B2%E6%A0%B8%E8%AF%95%E5%89%82%2C%E5%AF%B9MBH%E7%A2%B3%E9%85%B8%E9%85%AF%E7%9A%84%E4%B8 % 8D%E5%AF%B9%E7%A7%B0%E7%83%AF%E4%B8%99%E5%9F%BA%E7%A1%85%E9%86%9A%E5%8C%96%E5%8F%8D%E5%BA%94%E4%BB%8E%E5 % 82%AC%E5%8C%96%E5%89%82%E7%BB%93%E6%9E%84%2C%E7%A2%B1%E7%9A%84%E7%A7%8D%E7%B1%BB%2C%E5%8F%8D%E5%BA%94%E5 % BA%95%E7%89%A9%E7%9A%84%E6%AF%94%E4%BE%8B%2C%E6%BA%B6%E5%89%82%2C%E6%B8%A9%E5%BA%A6%E7%AD%89%E6%96%B9%E9 % 9DA2A2E88A1C, including the side of BF9DA2E88A1I, including BF9DA2E888A1, BF9A2E888A1, BF9A2E888A8, BF2, A2E88A8, BF7A2E88A8, BF2, A2E88A8, BF2, 96E5898228DHQD92PYR7, right, right. E4B8B _ 8B _ 8B _ 8B _ 8F _ 9B _ 8F _ 9B _ _ _ and _ _ _ 941220h2C83F2C83B899, including the following aspects: E883FI, E883F899, E590, E589, E789, 889, E789, 890, 889, E789, 889, and E883F73F899, right, right. 97E588B0911D, including the head of the bank, E588B091I, the head of the bank, E68E78A9E98E990A025E7872E990A025E7882, E790A025E782, including the head of BAE788B091, and the side of B7E78A9E9E980A7E5%, including the side of B7E78C90A08E78E78E78E780A780A7 E5%. 92%8C%E5%A4%A7%E4%BA%8E20%3A1%E7%9A%84%E5%8C%BA%E5%9F%9F%E9%80%89%E6%8B%A9%E6%80%A7.%E5%9C%A8%E4%BC%98%E5%8C % 96%E7%9A%84%E6%9D%A1%E4%BB%B6%E4%B8%8B%2C%E4%B8%80%E7%B3%BB%E5%88%97%E7%9A%84%E8%8A%B3%E7%8E%AF%2C%E6%9D % 82%E7%8E%AF%2C%E8%84%82%E8%82%AA%E6%97%8FMBH%E7%A2%B3%E9%85%B8%E9%85%AF%2825%E4%B8%AA%E5%8C%96%E5%90%88%E7%89 % A9%29%E8%83%BD%E5%A4%9F%E5%92%8C%E4%B8%89%E8%8B%AF%E5%9F%BA%E7%A1%85%E9%86%87%E5%BE%97%E5%88%B0%E4%B8%AD % E7%AD%89%E5%88%B0%E9%AB%98%E7%9A%84%E6%94%B6%E7%8E%87%28up%20to%2098%25%29%2C%E4%BC%98%E5%BC%82%E7%9A%84%E5%8C % BA%E5%9F%9F%E9%80%89%E6%8B%A9%E6%80%A7%2820%3A1%29%E4%BB%A5%E5%8F%8A%E5%A5%BD%E7%9A%84%E5%AF%B9%E6%98%A0%E9 8089E6B8B8B728upm: 8089B8B8B728up. you have the right side of your charge, including the following: 882%. You have the following side: 20 to 20: 00 to 20: 92, and to the other side, E697, B6, 882, and 20 to 20, 89, 89, 82, 82, 80, 89, 82, 80, 89, 82, 80, 89, 82, 82, 80, 89, 82, 80, 89, 82, 82, 80, 89, 82, 80, 89, 82, 82, 80, 8089, 882, and 2CE5E58F8F8D8D8D8D8F8F8D8D8F8F8D8F8D8F8D8F8D8D8D8F8F8D8D8F8D8F8D8D8F8F8D8D8D8F8D8F88F8D8F8F8D8F8F8D8D8F8F8D8F8F8F8D8F8D8F88F8D8D8D8F8D8F8F8F8F8D8F88F8D8F8 84%E5%AF%B9%E6%98%A0%E9%80%89%E6%8B%A9%E6%80%A7.%E9%9A%8F%E5%90%8E%E5%AF%B9%E4%BA%A7%E7%89%A9%E8%BF%9B%E8 % A18CE82222222% A18CE428D 8A784 E784 E719687D, E684E784E8E69687, E684, E794, E69687, right, side by side, right, right. B6E5, B7B7F8C8B5B5B7C7A5B5B5B5B7B7A7B, including the side of B6E582ACE582ACE5%, including the side of B6E5, B5B7B7F7F88B5B5888882A582ACE5%, including B6E590E582ACE5%. 8C8C96E58982, 8C882, E98882, E58889, 8C882, E88889, E589882, and E588889A8889A8889A8889A8888A8889A88889A888C969FBAE783AFB0E78A58FBAE783AFE8A58FBAE7E73AFE58A58FBAE78A58A588E88E888A888 E58F8F8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D8D88F884F884F884F84F8D88D8D8D8D8D8D8D8D8F8F88F84F88F84F84F84F84F84F84F8D8D8D8D8D8D8D8D8D88F88F88F88F88F88F88F8 94A8E8E4B4N9C8A8E4E4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4B4A888E4E8888B4B4B4B4B4B4B4B4A8888B4B0B48B4B4B4A88888B4B0B4B4B4B48B4B4B4B4B4 E588B0B0E689, E588B0E689, E588B0E689E689A7, including E8808C8C8C8E8E884, E8808C84E8808C894, E8%, and E88088C894 E8%, including E88808C894 E894 E8%, including E8808C884, E894, E8%, should be held. BF%98%E8%83%BD%E5%BE%97%E5%88%B0%E4%B8%80%E7%B3%BB%E5%88%97%E5%90%AB%E7%A1%85%E7%9A%84%E6%89%8B%E6%80%A7% E5%8C%96%E5%90%88%E7%89%A9.%E6%96%87%E7%AB%A0%E4%B8%AD%E6%96%B0%E5%90%88%E6%88%90%E7%9A%84%E6%B2%A1%E6%9C % 89%E6%96%87%E7%8C%AE%E8%A1%A8%E5%BE%81%E8%BF%87%E7%9A%84%E5%8C%96%E5%90%88%E7%89%A9%E9%83%BD%E8%BF%9B%E8 % A18C8C8CE8C3C13 A8C8C8C8C7E8E584 A81CE7BB8A8A8A8A8NMR8A8NMR8A7E7A8A8A8A8A8A7A8A8A8NRMSE8A8A8A8A7A8A8A7A8A8A7A8A8A7A8A7A8A7A8A7A8A7A8A7A8A7A8A1A1A1A1A1A1A1A1A1A1A1A1A1. E93A83C8C8C8C8C8C8C8C8C8C8C8C8C8C8A983A83A83C8C8C8C8C8A888A88A88A883A83A83C8C8C8C8C8C8A888A89A889 E589E589E589E589E589E589E589 and E588D95E596I and E5888D95E8C96I have the right side. 9BE8A8A18A8E8E8D8E699, E5E9E9AA8C7A1A1AE5E5E8A8DE8D8D8D8E5D8D8E8E5D8E8C96E59088E96E7E7A1A5E5E9A9A8A8A8A8A8D8A8E5D8D8E8E8D8D8D8E6D8C96E59088E96E7E7%. 89A9E9E9E9E5D E5AFB 9% E6 and 9 E84 were about 8Bs.
【学位授予单位】：河南师范大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.251
【参考文献】
相关期刊论文 前1条
1 ;Enantioselective O-allylic alkylation of Morita-Baylis-Hillman carbonates with oxime[J];Science in China(Series B:Chemistry);2009年09期
，本文编号：2300376
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