Synthesis 2015; 47(06): 875-886
DOI: 10.1055/s-0034-1379956
paper
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Organocatalytic Aza-Michael Reactions of Isatin Derivatives

Sergei Žari
Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia   Email: tonis.kanger@ttu.ee
,
Andrus Metsala
Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia   Email: tonis.kanger@ttu.ee
,
Marina Kudrjashova
Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia   Email: tonis.kanger@ttu.ee
,
Sandra Kaabel
Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia   Email: tonis.kanger@ttu.ee
,
Ivar Järving
Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia   Email: tonis.kanger@ttu.ee
,
Tõnis Kanger*
Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia   Email: tonis.kanger@ttu.ee
› Author Affiliations
Further Information

Publication History

Received: 05 November 2014

Accepted after revision: 05 December 2014

Publication Date:
14 January 2015 (online)


Abstract

Isatin was activated by derivatization to a Schiff base with aniline and used as an aza-Michael donor in organocatalytic asymmetric reactions with symmetric and nonsymmetric unsaturated 1,4-diketones. After hydrolysis (in situ), the N-substituted isatins were obtained in high yields (up to >95%) with high enantioselectivity (up to 95%).

Supporting Information

 
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