Synlett
DOI: 10.1055/a-1741-9069
synpacts

Development of an Aza-Piancatelli-Templated Reaction Manifold from 4-Aminocyclopentenones: Access to Complex Carbocyclic Assemblies

Chenna Jagadeesh
,
Biplab Mondal
,
Jaideep Saha
This work was supported by the Science and Engineering Research Board (SERB, CRG/2020/000381) and the Council of Scientific and Industrial Research, India (CSIR-EMR-II, 02(0395)/21/EMR-II) research grants to JS. CJ and BM thank UGC and CSIR for fellowships.


Abstract

Capitalizing on the propensity of 1,2-amino group migration in γ-aminocyclopentenone with a suitable promoter, gem-diaryl-equipped systems unfolded an unprecedented avenue for the Lewis acid promoted displacement of γ-aniline group with nucleophiles such as indole. Such transformation, besides providing a means for direct γ-functionalization of cyclopentenones, presented innumerable scope for β,γ-annulation. Various tailored indolo bisnucleophiles were explored in the current study that rendered an array of indole alkaloid-like compounds in excellent yields and selectivity through one-pot operation. Analysis of collective experimental observation along with designed control experiments strongly suggested the possibility of a retro aza-Piancatelli rearrangement, which is hitherto unknown in the context. Such repertoire could find potential applications in the synthesis of complex assemblies from the Piancatelli rearrangement and related processes.

1 Introduction

2 Aza-Piancatelli Rearrangement and Related Domino Processes

3 An Unprecedented Aza-Piancatelli-Templated Strategy for Polycyclic Assemblies

4 Summary and Outlook



Publication History

Received: 31 December 2021

Accepted after revision: 16 January 2022

Publication Date:
16 January 2022 (online)

© 2022. Thieme. All rights reserved

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