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Efficient and Stereoselective Rearrangement of Baylis-Hillman Acetates Catalyzed by Gold(I) Chloride/Silver(I) Trifluoromethanesulfonate

Yunkui Liu, Dajie Mao, Jianqiang Qian, Shaojie Lou, Zhenyuan Xu*, Yongmin Zhang

*State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou, 310014, P. R. of China, Email:

Y. Liu, D. Mao, J. Qian, S. Lou, Z. Xu, Y. Zhang, Synthesis, 2009, 1170-1174.

DOI: 10.1055/s-0028-1087971

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Efficient and stereoselective rearrangement catalyzed by only one mole-percent gold(I) chloride/silver(I) trifluoromethanesulfonate of Baylis-Hillman acetates afforded 2-(acetoxymethyl)alk-2-enoates under mild reaction conditions in very good yields with 100% E-selectivity.Cyclohex-2-enone derived Baylis-Hillman acetates gave 2-alkylidenecyclohex-3-enones by elimination of acetic acid.

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Key Words

gold/silver catalysis, stereoselectivity, rearrangements, Baylis-Hillman acetates, alk-2-enoates, unsaturated esters, allylic alcohols

ID: J66-Y2009-1140