Asymmetric 1,4-disubstitution of 1,3-dienes: Palladium(II)-catalyzed formation of azido-ketones from 1,3-cyclohexadiene
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- 作者：Arab K. El-Qisairi ; Hanan A. Qaseer ; Jeffrey P. Fennelly ; M. Paul Chiarelli ; Patrick M. Henry
- 关键词：Palladium(II) ; Cyclohexadiene ; Oxidation ; Azide ; Ketone ; Asymmetric
- 刊名：Catalysis Communications
- 出版年：2008
- 出版时间：1 April 2008
- 年：2008
- 卷：9
- 期：7
- 页码：1661-1665
- 全文大小：145 K
文摘
The oxidation of cyclohexadiene in a mixed aqueous solvent in the present of azide ion produced 4-azido-2-cyclohexene-1-one, 1, and 2-azido-3-cyclohexene-1-one, 2, in a four electron transfer in about a 70 % yield. The overall reaction is a net air oxidation. These enantioselectivies are higher than any obtained previously for addition to 1,3-dienes. The conversion of 1 to 2 involves a [3,3]sigmatropic rearrangement.