Issue 6, 2011
From the journal:

Organic & Biomolecular Chemistry

Efficient palladium-catalyzed asymmetric allylic alkylation of ketones and aldehydes†

Xiaohu Zhao,a   Delong Liu,b   Fang Xie,a   Yangang Liub  and  Wanbin Zhang*ab  

* Corresponding authors

a School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. China

b School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. China

Abstract

Palladium-catalyzed asymmetric allylic alkylation of ketones, via enamines generated in situ as nucleophiles, were carried out smoothly with chiral metallocene-based P,N-ligands. Under the same conditions, however, reactions of aldehydes could hardly be observed. Subsequently, this obstacle was resolved by using chiral metallocene-based P,P-ligands. Both ketones and aldehydes afforded excellent enantioselectivities with up to 98% ee and 94% ee, respectively.

Graphical abstract: Efficient palladium-catalyzed asymmetric allylic alkylation of ketones and aldehydes

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Article information

DOI
https://doi.org/10.1039/C0OB00915F
Article type
Paper
Submitted
21 Oct 2010
Accepted
13 Dec 2010
First published
15 Dec 2010

Org. Biomol. Chem., 2011,9, 1871-1875

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Efficient palladium-catalyzed asymmetric allylic alkylation of ketones and aldehydes

X. Zhao, D. Liu, F. Xie, Y. Liu and W. Zhang, Org. Biomol. Chem., 2011, 9, 1871 DOI: 10.1039/C0OB00915F

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