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Catalytic Allylation of Stabilized Phosphonium Ylides with Primary Allylic Amines

Xian-Tao Ma, Yong Wang, Rui-Han Dai, Cong-Rong Liu and Shi-Kai Tian*

*Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China, Email: tianskustc.edu.cn

X.-T. Ma, Y. Wang, R.-H. Dai, C.-R. Liu, S.-K. Tian, J. Org. Chem., 2013, 78, 11071-11075.

DOI: 10.1021/jo401736k (free Supporting Information)


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Abstract

Ketone-stabilized phosphonium ylides were allylated with high regioselectivity by primary allylic amines in the presence of 5 mol % Pd(PPh3)4 and 10 mol % B(OH)3. A subsequent one-pot Wittig olefination gave structurally diverse α,β-unsaturated ketones in good to excellent overall yields. Ester- and nitrile-stabilized phosphonium ylides can be converted if B(OH)3 is replaced with TsOH.

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Key Words

1,4-dienes, enones


ID: J42-Y2013