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Atroposelective Synthesis of 3,3’‐Bisindoles Bearing Axial and Central Chirality: Using Isatin‐Derived Imines as Electrophiles

Atroposelective Synthesis of 3,3’‐Bisindoles Bearing Axial and Central Chirality: Using... An atroposelective synthesis of a new class of 3,3’‐bisindoles bearing axial and central chirality has been established via catalytic asymmetric addition reactions using isatin‐derived imines as electrophiles (23 examples, up to 80% yield, > 95 : 5 dr, 98 : 2 er). This approach takes advantage of chiral phosphoric acid‐catalyzed dynamic kinetic resolution of 2‐substituted 3,3’‐bisindoles via nucleophilic addition of such substrates with isatin‐derived imines. In this approach, isatin‐derived imines acted as a class of competent electrophiles due to their high reactivity and bulky size, which provided an easy access to axially chiral 3,3'‐bisindoles incorporated with a biologically important chiral 3‐aminooxindole unit. This approach has greatly expanded the generality and applicability of the strategy of dynamic kinetic resolution for the synthesis of enantioenriched 3,3’‐bisindole derivatives bearing both axial and central chirality. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chinese Journal of Chemistry Wiley

Atroposelective Synthesis of 3,3’‐Bisindoles Bearing Axial and Central Chirality: Using Isatin‐Derived Imines as Electrophiles

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References (76)

Publisher
Wiley
Copyright
© 2020 SIOC, CAS, Shanghai & WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
1001-604X
eISSN
1614-7065
DOI
10.1002/cjoc.202000022
Publisher site
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Abstract

An atroposelective synthesis of a new class of 3,3’‐bisindoles bearing axial and central chirality has been established via catalytic asymmetric addition reactions using isatin‐derived imines as electrophiles (23 examples, up to 80% yield, > 95 : 5 dr, 98 : 2 er). This approach takes advantage of chiral phosphoric acid‐catalyzed dynamic kinetic resolution of 2‐substituted 3,3’‐bisindoles via nucleophilic addition of such substrates with isatin‐derived imines. In this approach, isatin‐derived imines acted as a class of competent electrophiles due to their high reactivity and bulky size, which provided an easy access to axially chiral 3,3'‐bisindoles incorporated with a biologically important chiral 3‐aminooxindole unit. This approach has greatly expanded the generality and applicability of the strategy of dynamic kinetic resolution for the synthesis of enantioenriched 3,3’‐bisindole derivatives bearing both axial and central chirality.

Journal

Chinese Journal of Chemistry – Wiley

Published: Jun 1, 2020

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