Exploring structural effects of ketone catalysts on asymmetric epoxidation of olefins
Exploring structural effects of ketone catalysts on asymmetric epoxidation of olefins
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DOI：
10.1016/j.tet.2005.03.123
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发表时间：
2005-06-27
期刊：
影响因子：
2.1
通讯作者：
Shi, Y
中科院分区：
文献类型：
--
作者：
Crane, Z;Goeddel, D;Shi, Y
研究了几种含螺醚和内酯的酮催化剂在烯烃不对称环氧化反应中的催化性能。结果表明，酮催化剂螺环上的取代基对对映选择性有较大的影响。研究结果还表明，共轭顺式烯烃与含恶唑啉酮酮的酮的高对映选择性可能部分归因于烯烃的R-pi基团与恶唑烷酮的羰基之间的吸引相互作用。此外，非键相互作用如货车德瓦尔斯力和/或恶唑烷酮的油精取代基和氮取代基之间的疏水相互作用也可参与立体分化。所获得的信息为酮催化环氧化反应的重要因素提供了额外的理解。(c)2005爱思唯尔有限公司保留所有权利。
Several ketone catalysts containing spiro ethers and lactones have been investigated for the asymmetric epoxidation of olefins. The results showed that substituents on the spiro ring of the ketone catalysts have profound effects on enantioselectivity. Results also suggested that the high enantioselectivities previously observed for conjugated cis-olefins with oxazoliclinone containing ketones Could he partially due to attractive interactions between the R-pi group of the olefin and the carbonyl group of the oxazolidinone. In addition, nonbonding interactions such as van der Waals forces and/or hydrophobic interactions between the oletin substituents and the nitrogen substituents of the oxazolidinone may also be involved in stereodifferentiation. The inforniation gained provides additional understanding of factors important for ketone catalyzed epoxidations. (c) 2005 Elsevier Ltd. All rights reserved.