Clean Inversion of Configuration in the Pd-Catalyzed Cross-Coupling of 2-Bromo-1,3-dienes
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- 作者：Xingzhong Zeng ; Qian Hu ; Mingxing Qian ; and Ei-ichi Negishi
- 刊名：Journal of the American Chemical Society
- 出版年：2003
- 出版时间：November 12, 2003
- 年：2003
- 卷：125
- 期：45
- 页码：13636 - 13637
- 全文大小：68K
- 年卷期：v.125,no.45(November 12, 2003)
- ISSN：1520-5126
文摘
The Pd-catalyzed cross-coupling reaction of 2-bromo-1,3-dienes derived from alkyl aldehydes, especially with Cl2Pd(DPEphos) as a catalyst, proceeds with clean stereoinversion of the Br-bearing C=C bond to produce in high yields and in high stereoselectivity (
97-98%) conjugated Z,E dienes of potentially high utility in the synthesis of complex natural products. The observed stereoinversion cannot be readily accommodated by the widely accepted 
-
- rearrangement mechanism for isomerization of ordinary allylpalladium derivatives.
97-98%) conjugated Z,E dienes of potentially high utility in the synthesis of complex natural products. The observed stereoinversion cannot be readily accommodated by the widely accepted -- rearrangement mechanism for isomerization of ordinary allylpalladium derivatives.