The facile dearomatization of nitroaromatic compounds using lithium enolates of unsaturated ketones in conjugate additions and (4+2) formal cycloadditions

Karine Pasturaud; Batoul Rkein; Morgane Sanselme; Muriel Sebban; Sami Lakhdar; Muriel Durandetti; Julien Legros; Isabelle Chataigner

doi:10.1039/c9cc02924a

The facile dearomatization of nitroaromatic compounds using lithium enolates of unsaturated ketones in conjugate additions and (4+2) formal cycloadditions

Karine Pasturaud
, Batoul Rkein
, Morgane Sanselme
, Muriel Sebban
, Sami Lakhdar
, Muriel Durandetti
, Julien Legros
, Isabelle Chataigner

Normandie Université
Normandie Université

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

18 Citations (Scopus)

Abstract

The dearomatization of conventional nitroarenes by lithiated enolates derived from methyl vinyl ketones easily takes place, following a formal (4+2) cycloaddition process. While nitroindoles react readily with in situ generated conjugated enolates, the deaggregation of these latter species using HMPA extends the reaction scope to the more aromatic nitronaphthalenes and pyridines.

Original language	English
Pages (from-to)	7494-7497
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	52
DOIs	https://doi.org/10.1039/c9cc02924a
Publication status	Published - 1 Jan 2019
Externally published	Yes

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abstract = "The dearomatization of conventional nitroarenes by lithiated enolates derived from methyl vinyl ketones easily takes place, following a formal (4+2) cycloaddition process. While nitroindoles react readily with in situ generated conjugated enolates, the deaggregation of these latter species using HMPA extends the reaction scope to the more aromatic nitronaphthalenes and pyridines.",

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AU - Pasturaud, Karine

AU - Rkein, Batoul

AU - Sanselme, Morgane

AU - Sebban, Muriel

AU - Lakhdar, Sami

AU - Durandetti, Muriel

AU - Legros, Julien

AU - Chataigner, Isabelle

PY - 2019/1/1

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AB - The dearomatization of conventional nitroarenes by lithiated enolates derived from methyl vinyl ketones easily takes place, following a formal (4+2) cycloaddition process. While nitroindoles react readily with in situ generated conjugated enolates, the deaggregation of these latter species using HMPA extends the reaction scope to the more aromatic nitronaphthalenes and pyridines.

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U2 - 10.1039/c9cc02924a

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ER -

The facile dearomatization of nitroaromatic compounds using lithium enolates of unsaturated ketones in conjugate additions and (4+2) formal cycloadditions

Abstract

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