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Diels–Alder dimerization of Morita–Baylis–Hillman acetates catalyzed by organocatalysts

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Abstract

DABCO-catalyzed dimerization of Morita–Baylis–Hillman acetates to synthesize a series of 3-alkyl-4-(E)-alkenyl-cyclohex-1-ene-1,4-dicarbonyl compounds in excellent yields with modest to excellent diastereoselectivity is reported. A plausible reaction mechanism is also proposed on the basis of previous literature and preliminary investigation the asymmetric version of the reaction.

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Acknowledgments

We thank the Shanghai Municipal Committee of Science and Technology (08dj1400100-2), National Basic Research Program of China (973)-2010CB833302, the Fundamental Research Funds for the Central Universities and the National Natural Science Foundation of China for financial support (21072206, 20472096, 20872162, 20672127, 20821002 and 20732008).

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  1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, 200032, China

    Hong-Ping Deng, Yin Wei & Min Shi

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  1. Hong-Ping Deng
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  2. Yin Wei
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Correspondence to Min Shi.

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Deng, HP., Wei, Y. & Shi, M. Diels–Alder dimerization of Morita–Baylis–Hillman acetates catalyzed by organocatalysts. Res Chem Intermed 39, 5–18 (2013). https://doi.org/10.1007/s11164-012-0626-6

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