Aza-conjugate addition methodology for the synthesis of N-hydroxy-isoindolin-1-ones

Santiago Royo; Robert S L Chapman; Alisia M. Sim; Lucy R. Peacock; Steven D. Bull

doi:10.1021/acs.orglett.6b00261

Aza-conjugate addition methodology for the synthesis of N-hydroxy-isoindolin-1-ones

Santiago Royo, Robert S L Chapman, Alisia M. Sim, Lucy R. Peacock, Steven D. Bull

Department of Chemistry

Universitat Jaume I

Research output: Contribution to journal › Article › peer-review

25 Citations (SciVal)

Abstract

Aryl-aldehydes containing ortho-substituted propiolate fragments react with hydroxylamine to afford carbinolamine intermediates that undergo intramolecular aza-conjugate addition reactions to afford N-hydroxy-2.3-dihydro-isoindolin-1-ones that can be reduced to their corresponding isoindolin-1-ones and isoindoles.

Original language	English
Pages (from-to)	1146-1149
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	5
Early online date	22 Feb 2016
DOIs	https://doi.org/10.1021/acs.orglett.6b00261
Publication status	Published - 4 Mar 2016

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title = "Aza-conjugate addition methodology for the synthesis of N-hydroxy-isoindolin-1-ones",

abstract = "Aryl-aldehydes containing ortho-substituted propiolate fragments react with hydroxylamine to afford carbinolamine intermediates that undergo intramolecular aza-conjugate addition reactions to afford N-hydroxy-2.3-dihydro-isoindolin-1-ones that can be reduced to their corresponding isoindolin-1-ones and isoindoles.",

author = "Santiago Royo and Chapman, {Robert S L} and Sim, {Alisia M.} and Peacock, {Lucy R.} and Bull, {Steven D.}",

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AU - Royo, Santiago

AU - Chapman, Robert S L

AU - Sim, Alisia M.

AU - Peacock, Lucy R.

AU - Bull, Steven D.

PY - 2016/3/4

Y1 - 2016/3/4

N2 - Aryl-aldehydes containing ortho-substituted propiolate fragments react with hydroxylamine to afford carbinolamine intermediates that undergo intramolecular aza-conjugate addition reactions to afford N-hydroxy-2.3-dihydro-isoindolin-1-ones that can be reduced to their corresponding isoindolin-1-ones and isoindoles.

AB - Aryl-aldehydes containing ortho-substituted propiolate fragments react with hydroxylamine to afford carbinolamine intermediates that undergo intramolecular aza-conjugate addition reactions to afford N-hydroxy-2.3-dihydro-isoindolin-1-ones that can be reduced to their corresponding isoindolin-1-ones and isoindoles.

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ER -

Aza-conjugate addition methodology for the synthesis of N-hydroxy-isoindolin-1-ones

Abstract

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