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Issue 34, 2015
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An enantioselective organocatalyzed aza-Morita–Baylis–Hillman reaction of isatin-derived ketimines with acrolein

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Abstract

A highly enantioselective aza-Morita–Baylis–Hillman (aza-MBH) reaction of isatin-derived ketimines with acrolein was established using β-isocupreidine (β-ICD) or α-isocupreine (α-ICPN) as a chiral acid–base organocatalyst. The present protocol readily furnished (S) or (R)-aza-MBH adducts with a chiral tetrasubstituted carbon stereogenic center in up to 98% ee.

Graphical abstract: An enantioselective organocatalyzed aza-Morita–Baylis–Hillman reaction of isatin-derived ketimines with acrolein

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Publication details

The article was received on 30 Apr 2015, accepted on 17 Jul 2015 and first published on 17 Jul 2015


Article type: Paper
DOI: 10.1039/C5OB00874C
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Org. Biomol. Chem., 2015,13, 9022-9028

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    An enantioselective organocatalyzed aza-Morita–Baylis–Hillman reaction of isatin-derived ketimines with acrolein

    Y. Yoshida, M. Sako, K. Kishi, H. Sasai, S. Hatakeyama and S. Takizawa, Org. Biomol. Chem., 2015, 13, 9022
    DOI: 10.1039/C5OB00874C

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