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General and Highly α-Regioselective Zinc-Mediated Prenylation of Aldehydes and Ketones

Li-Ming Zhao*, Hai-Shan Jin, Li-Jing Wan and Li-Ming Zhang

*School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, Jiangsu, China, Email: lmzhaoxznu.edu.cn

L.-M. Zhao, H.-S. Jin, L.-J. Wan, L.-M. Zhang, J. Org. Chem., 2011, 76, 1831-1837.

DOI: 10.1021/jo102516a (free Supporting Information)


Abstract

A wide range of α-prenylated alcohol derivatives could be obtained in good yields by highly α-regioselective zinc-mediated prenylation of various aldehydes and ketones with prenyl bromide at 120C in HMPA. By simply altering the reaciton solvent and temperature, the method allows the achievement of a highly notable opposite regiocontrol, providing the expected regiochemical product.

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Key Words

1,2-Addition


ID: J42-Y2011-0720