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Synfacts 2010(12): 1422-1422  
DOI: 10.1055/s-0030-1258927
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Morita-Baylis-Hillman Reactions of Acrolein

Contributor(s): Benjamin List, Saihu Liao
Y.-L. Liu, B.-L. Wang, J.-J. Cao, L. Chen, Y.-X. Zhang, C. Wang, J. Zhou*
East China Normal University, Shanghai, P. R. of China
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Publication History

Publication Date:
22 November 2010 (online)

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Significance

A highly enantioselective Morita-Baylis-Hillman (MBH) reaction using ketones as electrophiles has been realized in the addition of acrolein 2 to indole-2,3-diones (isatins, 1). In the presence of Hatakeyama-type β-isocupreidine 3, the reactions of 1 and 2 gave adducts 4 in good yields with excellent stereocontrol (er from 95:5 to 99:1). Unprotected, N-methyl- and N-benzyl-protected isatins 1 gave high levels of enantioselectivities, though lower yields were obtained with ­unprotected ones due to their poor solubility in dichloromethane. One example employing ethyl acrylate as the nucleophile was also shown and good yield and an er of 98:2 were obtained.