Efficient construction of a chiral all-carbon quaternary center by asymmetric 1,4-addition and its application to total synthesis of (+)-bakuchiol
Efficient construction of a chiral all-carbon quaternary center by asymmetric 1,4-addition and its application to total synthesis of (+)-bakuchiol
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DOI：
10.1016/j.tetlet.2008.09.106
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发表时间：
2008-11-24
影响因子：
1.8
通讯作者：
Fukuyama, Yoshiyasu
中科院分区：
文献类型：
--
作者：
Esumi, Tomoyuki;Shimizu, Hiroyuki;Fukuyama, Yoshiyasu
二乙烯基铜酸锂与(4S,2'E)-3-(6'-TBDPS-3'-甲基己-2'-烯酰基)-4-苯基恶唑烷-2-酮的共轭加成有效地进行，产生具有高非对映选择性的手性全碳四元中心(R:S = 95:5)。通过将该方法应用于(+)-补骨脂酚的全合成，证实了新生成的手性中心的绝对构型。 (c) 2008 Elsevier Ltd. 保留所有权利。
The conjugate addition of lithium divinylcuprate to (4S,2'E)-3-(6'-TBDPS-3'-methylhex-2'-enoyl)-4-phenyloxazolidin-2-one proceeded efficiently to create a chiral all-carbon quaternary center with a high diastereoselectivity (R:S = 95:5). The absolute configuration of the newly generated chiral center was confirmed by applying this methodology to the total synthesis of (+)-bakuchiol. (c) 2008 Elsevier Ltd. All rights reserved.