Maleimide as an efficient nucleophilic partner in the aza-Morita-Baylis-Hillman reaction: synthesis of chiral 3-substituted-3-aminooxindoles

Organic & Biomolecular Chemistry
Akshay KumarSwapandeep Singh Chimni

Abstract

A highly enantioselective Morita-Baylis-Hillman reaction of maleimides with isatin derived ketimines has been developed to obtain enantiomerically enriched 3-substituted-3-aminooxindoles using β-isocupreidine as an organocatalyst. Maleimide acting as a nucleophile provides products with up to 99% ee.

References

Apr 3, 2007·Angewandte Chemie·Géraldine MassonJieping Zhu
Jan 15, 2009·Chemical Reviews·Valérie DeclerckFrédéric Lamaty
Jun 10, 2010·Chemistry : a European Journal·Pankaj Chauhan, Swapandeep Singh Chimni
Aug 26, 2010·Chemical Reviews·Deevi BasavaiahSatpal Singh Badsara
Jan 13, 2012·Organic & Biomolecular Chemistry·Andrea MazzantiRamon Rios
May 29, 2012·Bioorganic & Medicinal Chemistry·Claudio G Lima-Junior, Mário L A A Vasconcellos
Oct 24, 2012·Chemical Communications : Chem Comm·Yun-Lin Liu, Jian Zhou
Aug 14, 2013·Chemical Communications : Chem Comm·Shinobu TakizawaHiroaki Sasai
Jul 6, 2014·Beilstein Journal of Organic Chemistry·Akshay Kumar, Swapandeep Singh Chimni

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Citations

Jun 9, 2016·Organic & Biomolecular Chemistry·Bo-Liang ZhaoDa-Ming Du
Jul 28, 2015·Organic & Biomolecular Chemistry·Yasushi YoshidaShinobu Takizawa
Jul 26, 2019·Organic & Biomolecular Chemistry·Michael FrancJan Veselý
Mar 16, 2016·Beilstein Journal of Organic Chemistry·Qing HeYing-Chun Chen
Aug 30, 2017·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Jasneet KaurSwapandeep Singh Chimni

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