Synlett 2012; 23(12): 1805-1808
DOI: 10.1055/s-0031-1290404
letter
© Georg Thieme Verlag Stuttgart · New York

‘Evans Auxiliary’ Based P–N Ligands for Pd-Catalyzed Asymmetric Allylic Alkylation Reactions

Yun Li
a   China Novartis Institutes for BioMedical Research Co.,Ltd. , Building 8, Lane 898 Halei Road, 201203, Shanghai, P. R. of China
,
Fang Liang
a   China Novartis Institutes for BioMedical Research Co.,Ltd. , Building 8, Lane 898 Halei Road, 201203, Shanghai, P. R. of China
,
Rui Wu
a   China Novartis Institutes for BioMedical Research Co.,Ltd. , Building 8, Lane 898 Halei Road, 201203, Shanghai, P. R. of China
,
Qian Li
a   China Novartis Institutes for BioMedical Research Co.,Ltd. , Building 8, Lane 898 Halei Road, 201203, Shanghai, P. R. of China
,
Quan-Rui Wang
b   Department of Chemistry, Fudan University, 220 Handan Road, 200433, Shanghai, P. R. of China, Fax: +86(21)61606155   Email: lei-1.jiang@novartis.com
,
Yao-Chang Xu
a   China Novartis Institutes for BioMedical Research Co.,Ltd. , Building 8, Lane 898 Halei Road, 201203, Shanghai, P. R. of China
,
Lei Jiang*
a   China Novartis Institutes for BioMedical Research Co.,Ltd. , Building 8, Lane 898 Halei Road, 201203, Shanghai, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 16 April 2012

Accepted after revision: 06 May 2012

Publication Date:
14 June 2012 (online)


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Abstract

A new type of chiral P–N ligands has been prepared which incorporates the Evans auxiliary as chiral ligand. They were found to act as effective ligands in the Pd-catalyzed allylic alkylation reactions. Using these ligands with allylpalladium chloride dimer as catalyst, the coupling of 1,3-diphenyl-3-acetoxyprop-1-ene and dimethyl malonate proceeded smoothly at –10 °C providing the desired product with enantiomeric excess up to 87% and excellent yield.

Supporting Information