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An organic-base catalyzed asymmetric 1,4-addition of tritylthiol to in situ generated aza-o-quinone methides at the H2O/DCM interface

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Abstract

Based on an efficient method for in situ generation of N-o-QM species in the presence of a base, enantioselective catalytic conjugated additions of tritylthiol to in situ generated N-o-QMs are reported. Acid–base bifunctional organocatalyst 4c (10 mol%) enables these transformations with high stereoselectivities (up to 94% ee) using H2O/DCM as a solvent under mild conditions.

Graphical abstract: An organic-base catalyzed asymmetric 1,4-addition of tritylthiol to in situ generated aza-o-quinone methides at the H2O/DCM interface

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Publication details

The article was received on 26 Nov 2018, accepted on 04 Feb 2019 and first published on 07 Feb 2019


Article type: Communication
DOI: 10.1039/C8CC09382B
Citation: Chem. Commun., 2019, Advance Article

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    An organic-base catalyzed asymmetric 1,4-addition of tritylthiol to in situ generated aza-o-quinone methides at the H2O/DCM interface

    X. Liu, K. Wang, W. Guo, Y. Liu and C. Li, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C8CC09382B

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