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Zhao BL, Lin Y, Yan HH, et al. Squaramide-catalysed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral trisubstituted pyrrolidines. Org Biomol Chem. 2015;13(46):11351-61doi: 10.1039/c5ob01749a.
Zhao, B. L., Lin, Y., Yan, H. H., & Du, D. M. (2015). Squaramide-catalysed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral trisubstituted pyrrolidines. Organic & biomolecular chemistry, 13(46), 11351-61. https://doi.org/10.1039/c5ob01749a
Zhao, Bo-Liang, et al. "Squaramide-catalysed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral trisubstituted pyrrolidines." Organic & biomolecular chemistry vol. 13,46 (2015): 11351-61. doi: https://doi.org/10.1039/c5ob01749a
Zhao BL, Lin Y, Yan HH, Du DM. Squaramide-catalysed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral trisubstituted pyrrolidines. Org Biomol Chem. 2015 Dec 14;13(46):11351-61. doi: 10.1039/c5ob01749a. PMID: 26426388.
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Org Biomol Chem. 2015 Dec 14;13(46):11351-61. doi: 10.1039/c5ob01749a.

Squaramide-catalysed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral trisubstituted pyrrolidines.

Organic & biomolecular chemistry

Bo-Liang Zhao, Ye Lin, Hao-Hao Yan, Da-Ming Du

Affiliations

  1. School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China. [email protected].
  2. School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China. [email protected] and State Key Laboratory of Elemento-Organic Chemistry, Nankai University.

PMID: 26426388 DOI: 10.1039/c5ob01749a

Abstract

A bifunctional squaramide catalysed aza-Michael/Michael cascade reaction between nitroalkenes and tosylaminomethyl enones or enoates has been developed. This organocatalytic cascade reaction provides easy access to highly functionalized chiral pyrrolidines with a broad substrate scope, giving the desired products in good yields (up to 99%) with good diastereoselectivities (up to 91 : 9 dr) and excellent enantioselectivities (up to >99% ee) under mild conditions. This protocol provides a straightforward entry to highly functionalized chiral trisubstituted pyrrolidine derivatives from simple starting materials.

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