铑（I）-二甲苯基-联萘酚膦催化的不对称烯酰胺-[2 + 2 + 2]环加成反应用于合成光学富集的N，O-二芳基化合物。
A Rhodium(I)-Xylyl-BINAP Catalyzed Asymmetric Ynamide-[2 + 2 + 2] Cycloaddition in the Synthesis of Optically Enriched N,O-Biaryls.
作者信息
Oppenheimer Jossian, Johnson Whitney L, Figueroa Ruth, Hayashi Ryuji, Hsung Richard P
机构信息
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, WI 53705 USA.
出版信息
Tetrahedron. 2009 Jun 27;65(26):5001-5012. doi: 10.1016/j.tet.2009.03.078.
Abstract
A rhodium(I)-xylyl-BINAP catalyzed asymmetric [2 + 2 + 2] cycloaddition of achiral conjugated aryl ynamides with various diynes is described here. This asymmetric cycloaddition provides a series of structurally interesting chiral N,O-biaryls with excellent enantioselectivity along with a modest diastereoselectivity with respect to both C-C and C-N axial chirality.
摘要
本文描述了一种铑（I）-二甲苯基-联萘酚（BINAP）催化的非手性共轭芳基炔酰胺与各种二炔的不对称[2 + 2 + 2]环加成反应。这种不对称环加成反应提供了一系列结构有趣的手性N，O-二芳基化合物，具有优异的对映选择性以及关于C-C和C-N轴手性的适度非对映选择性。
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3
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Org Lett. 2009 Feb 19;11(4):899-902. doi: 10.1021/ol802844z.
4
Application of ynamides in the synthesis of 2-amidoindoles.烯二炔酰胺在2-酰胺基吲哚合成中的应用。
Org Lett. 2009 Jan 1;11(1):221-4. doi: 10.1021/ol802477d.
5
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