RhIII-Catalyzed Oxidative Olefination of Vinylic C-H Bonds: Efficient and Selective Access to Di-unsaturated α-Amino Acid Derivatives and Other Linear 1,3-Butadienes

被引:219
作者
Besset, Tatiana [2 ]
Kuhl, Nadine [1 ]
Patureau, Frederic W. [1 ]
Glorius, Frank [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
[2] Univ Amsterdam, Vant Hoff Inst Mol Sci, NL-1098 XH Amsterdam, Netherlands
基金
欧洲研究理事会;
关键词
amino acids; butadienes; C-H activation; oxidative Heck-coupling; rhodium; CROSS-COUPLING REACTION; PD(II)-CATALYZED OLEFINATION; FUNCTIONALIZATION; ACTIVATION; ALKENYLATION; ALKYNES; INDOLES; ALKENES; ACRYLATES; ARENES;
D O I
10.1002/chem.201101340
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Olefin(s) get-together! A RhIII-catalyzed oxidative cross-coupling of different olefins was developed, resulting in the formation of valuable linear butadiene products and especially di-unsaturated α-amino acid derivatives. 1,1-Di-, 1,2-di-, and 1,1,2-trisubstituted olefins could be coupled with styrenes and acrylates. In these reactions, remarkably high levels of chemo-, regio-, and stereoselectivity were obtained, rendering this a valuable synthetic tool. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:7167 / 7171
页数:5
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