Literature DB >> 26214279

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

Yasushi Yoshida1, Makoto Sako, Kenta Kishi, Hiroaki Sasai, Susumi Hatakeyama, Shinobu Takizawa.   

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.

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Year:  2015        PMID: 26214279     DOI: 10.1039/c5ob00874c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  3 in total

Review 1.  Synthesis of chiral 3-substituted 3-amino-2-oxindoles through enantioselective catalytic nucleophilic additions to isatin imines.

Authors:  Hélène Pellissier
Journal:  Beilstein J Org Chem       Date:  2018-06-06       Impact factor: 2.883

Review 2.  Cupreines and cupreidines: an established class of bifunctional cinchona organocatalysts.

Authors:  Laura A Bryant; Rossana Fanelli; Alexander J A Cobb
Journal:  Beilstein J Org Chem       Date:  2016-03-07       Impact factor: 2.883

3.  Application of 7-azaisatins in enantioselective Morita-Baylis-Hillman reaction.

Authors:  Qing He; Gu Zhan; Wei Du; Ying-Chun Chen
Journal:  Beilstein J Org Chem       Date:  2016-02-18       Impact factor: 2.883

  3 in total

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