Issue 34, 2015

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

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

Supplementary files

Article information

Article type
Paper
Submitted
30 Apr 2015
Accepted
17 Jul 2015
First published
17 Jul 2015

Org. Biomol. Chem., 2015,13, 9022-9028

Author version available

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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