Palladium-Catalyzed Decarboxylative Formal (4 + 2) Cycloaddition of Vinyl Benzoxazinanones with 3-Nitroindoles

Melissa J. Bird; Steven M. Wales; Christopher Richardson; Christopher J.T. Hyland

doi:10.1055/s-0040-1707995

Palladium-Catalyzed Decarboxylative Formal (4 + 2) Cycloaddition of Vinyl Benzoxazinanones with 3-Nitroindoles

Melissa J. Bird, Steven M. Wales, Christopher Richardson, Christopher J.T. Hyland^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

14 Citations (Scopus)

Abstract

A diastereoselective palladium-catalyzed dearomative formal (4 + 2) cycloaddition between vinyl benzoxazinanones and 3-nitroindoles has been developed. This reaction provides a concise route to tetrahydro-5 H-indolo[2,3-b ]quinolines in excellent yield (up to 94%) and diastereoselectivity (up to >98:2), with versatile functional handles including vinyl, nitro, and free NH groups.

Original language	English
Article number	st-2010-r0641-l
Pages (from-to)	916-924
Number of pages	9
Journal	SYNLETT
Volume	31
Issue number	9
DOIs	https://doi.org/10.1055/s-0040-1707995
Publication status	Published - 3 Jun 2020

Bibliographical note

Funding Information:
The authors thank the University of Wollongong and the Australian Research Council (DP180101332) for the generous funding for this research.AustralianResearchCouncil(DP180101332)UniversityofWollongong()

Publisher Copyright:
© 2020. Thieme. All rights reserved.

Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.

Keywords

dearomatization
indoles
Pd catalysis
vinyl benzoxazinanones

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title = "Palladium-Catalyzed Decarboxylative Formal (4 + 2) Cycloaddition of Vinyl Benzoxazinanones with 3-Nitroindoles",

abstract = "A diastereoselective palladium-catalyzed dearomative formal (4 + 2) cycloaddition between vinyl benzoxazinanones and 3-nitroindoles has been developed. This reaction provides a concise route to tetrahydro-5 H-indolo[2,3-b ]quinolines in excellent yield (up to 94%) and diastereoselectivity (up to >98:2), with versatile functional handles including vinyl, nitro, and free NH groups.",

keywords = "dearomatization, indoles, Pd catalysis, vinyl benzoxazinanones",

author = "Bird, {Melissa J.} and Wales, {Steven M.} and Christopher Richardson and Hyland, {Christopher J.T.}",

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language = "English",

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AU - Wales, Steven M.

AU - Richardson, Christopher

AU - Hyland, Christopher J.T.

N1 - Funding Information: The authors thank the University of Wollongong and the Australian Research Council (DP180101332) for the generous funding for this research.AustralianResearchCouncil(DP180101332)UniversityofWollongong() Publisher Copyright: © 2020. Thieme. All rights reserved. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2020/6/3

Y1 - 2020/6/3

N2 - A diastereoselective palladium-catalyzed dearomative formal (4 + 2) cycloaddition between vinyl benzoxazinanones and 3-nitroindoles has been developed. This reaction provides a concise route to tetrahydro-5 H-indolo[2,3-b ]quinolines in excellent yield (up to 94%) and diastereoselectivity (up to >98:2), with versatile functional handles including vinyl, nitro, and free NH groups.

AB - A diastereoselective palladium-catalyzed dearomative formal (4 + 2) cycloaddition between vinyl benzoxazinanones and 3-nitroindoles has been developed. This reaction provides a concise route to tetrahydro-5 H-indolo[2,3-b ]quinolines in excellent yield (up to 94%) and diastereoselectivity (up to >98:2), with versatile functional handles including vinyl, nitro, and free NH groups.

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KW - indoles

KW - Pd catalysis

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ER -

Palladium-Catalyzed Decarboxylative Formal (4 + 2) Cycloaddition of Vinyl Benzoxazinanones with 3-Nitroindoles

Abstract

Bibliographical note

Keywords

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