Tandem Chiral Cu(II) Phosphate-Catalyzed Deoxygenation of Nitrones/Enantioselective Povarov Reaction with Enecarbamates

Coralie Gelis; Guillaume Levitre; Vincent Guérineau; David Touboul; Luc Neuville; Géraldine Masson

doi:10.1002/ejoc.201900547

Tandem Chiral Cu(II) Phosphate-Catalyzed Deoxygenation of Nitrones/Enantioselective Povarov Reaction with Enecarbamates

Coralie Gelis
, Guillaume Levitre
, Vincent Guérineau
, David Touboul
, Luc Neuville
, Géraldine Masson

Centre national de la recherche scientifique

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

Abstract

A new catalytic enantioselective tandem deoxygenation/aza-Diels-Alder reaction of nitrones with enecarbamates was serendipitously discovered in the presence of chiral copper(II) diphosphate complexes. This process affords a wide range of 4-aminotetrahydroquinolines in respectable yields under mild conditions with good to excellent ee values.

Original language	English
Pages (from-to)	5151-5155
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	31-32
DOIs	https://doi.org/10.1002/ejoc.201900547
Publication status	Published - 1 Sept 2019

Keywords

Aza-Diels-Alder reaction
Copper phosphate
Deoxygenation
Enecarbamate
Heterocycles

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10.1002/ejoc.201900547

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title = "Tandem Chiral Cu(II) Phosphate-Catalyzed Deoxygenation of Nitrones/Enantioselective Povarov Reaction with Enecarbamates",

abstract = "A new catalytic enantioselective tandem deoxygenation/aza-Diels-Alder reaction of nitrones with enecarbamates was serendipitously discovered in the presence of chiral copper(II) diphosphate complexes. This process affords a wide range of 4-aminotetrahydroquinolines in respectable yields under mild conditions with good to excellent ee values.",

keywords = "Aza-Diels-Alder reaction, Copper phosphate, Deoxygenation, Enecarbamate, Heterocycles",

author = "Coralie Gelis and Guillaume Levitre and Vincent Gu{\'e}rineau and David Touboul and Luc Neuville and G{\'e}raldine Masson",

note = "Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2019",

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day = "1",

doi = "10.1002/ejoc.201900547",

language = "English",

volume = "2019",

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journal = "European Journal of Organic Chemistry",

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T1 - Tandem Chiral Cu(II) Phosphate-Catalyzed Deoxygenation of Nitrones/Enantioselective Povarov Reaction with Enecarbamates

AU - Gelis, Coralie

AU - Levitre, Guillaume

AU - Guérineau, Vincent

AU - Touboul, David

AU - Neuville, Luc

AU - Masson, Géraldine

PY - 2019/9/1

Y1 - 2019/9/1

N2 - A new catalytic enantioselective tandem deoxygenation/aza-Diels-Alder reaction of nitrones with enecarbamates was serendipitously discovered in the presence of chiral copper(II) diphosphate complexes. This process affords a wide range of 4-aminotetrahydroquinolines in respectable yields under mild conditions with good to excellent ee values.

AB - A new catalytic enantioselective tandem deoxygenation/aza-Diels-Alder reaction of nitrones with enecarbamates was serendipitously discovered in the presence of chiral copper(II) diphosphate complexes. This process affords a wide range of 4-aminotetrahydroquinolines in respectable yields under mild conditions with good to excellent ee values.

KW - Aza-Diels-Alder reaction

KW - Copper phosphate

KW - Deoxygenation

KW - Enecarbamate

KW - Heterocycles

U2 - 10.1002/ejoc.201900547

DO - 10.1002/ejoc.201900547

M3 - Article

AN - SCOPUS:85067675601

SN - 1434-193X

VL - 2019

SP - 5151

EP - 5155

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 31-32

ER -

Tandem Chiral Cu(II) Phosphate-Catalyzed Deoxygenation of Nitrones/Enantioselective Povarov Reaction with Enecarbamates

Abstract

Keywords

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