Dual metal and Lewis base catalysis approach for asymmetric synthesis of dihydroquinolines and the α-arylation of aldehydes via N-acyliminium ions

Chandra M.R. Volla; Eleonora Fava; Iuliana Atodiresei; Magnus Rueping

doi:10.1039/c5cc05209b

Dual metal and Lewis base catalysis approach for asymmetric synthesis of dihydroquinolines and the α-arylation of aldehydes via N-acyliminium ions

Chandra M.R. Volla, Eleonora Fava, Iuliana Atodiresei, Magnus Rueping^*

^*Corresponding author for this work

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

30 Scopus citations

Abstract

A dual catalytic system consisting of indium triflate and a chiral imidazolidinone catalyzes the asymmetric addition of aldehydes to N-acyl quinoliniums furnishing optically active dihydroquinolines in good yields and excellent selectivities. The products were further functionalized into optically active tetrahydroquinolines, quinolines and 6-oxa-2-aza-bicyclo[3.3.1]nonanes.

Original language	English (US)
Pages (from-to)	15788-15791
Number of pages	4
Journal	CHEMICAL COMMUNICATIONS
Volume	51
Issue number	87
DOIs	https://doi.org/10.1039/c5cc05209b
State	Published - 2015
Externally published	Yes

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry 2015.

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c5cc05209b

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title = "Dual metal and Lewis base catalysis approach for asymmetric synthesis of dihydroquinolines and the α-arylation of aldehydes via N-acyliminium ions",

abstract = "A dual catalytic system consisting of indium triflate and a chiral imidazolidinone catalyzes the asymmetric addition of aldehydes to N-acyl quinoliniums furnishing optically active dihydroquinolines in good yields and excellent selectivities. The products were further functionalized into optically active tetrahydroquinolines, quinolines and 6-oxa-2-aza-bicyclo[3.3.1]nonanes.",

author = "Volla, {Chandra M.R.} and Eleonora Fava and Iuliana Atodiresei and Magnus Rueping",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2015.",

year = "2015",

doi = "10.1039/c5cc05209b",

language = "English (US)",

volume = "51",

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T1 - Dual metal and Lewis base catalysis approach for asymmetric synthesis of dihydroquinolines and the α-arylation of aldehydes via N-acyliminium ions

AU - Volla, Chandra M.R.

AU - Fava, Eleonora

AU - Atodiresei, Iuliana

AU - Rueping, Magnus

N1 - Publisher Copyright: © The Royal Society of Chemistry 2015.

PY - 2015

Y1 - 2015

N2 - A dual catalytic system consisting of indium triflate and a chiral imidazolidinone catalyzes the asymmetric addition of aldehydes to N-acyl quinoliniums furnishing optically active dihydroquinolines in good yields and excellent selectivities. The products were further functionalized into optically active tetrahydroquinolines, quinolines and 6-oxa-2-aza-bicyclo[3.3.1]nonanes.

AB - A dual catalytic system consisting of indium triflate and a chiral imidazolidinone catalyzes the asymmetric addition of aldehydes to N-acyl quinoliniums furnishing optically active dihydroquinolines in good yields and excellent selectivities. The products were further functionalized into optically active tetrahydroquinolines, quinolines and 6-oxa-2-aza-bicyclo[3.3.1]nonanes.

UR - http://www.scopus.com/inward/record.url?scp=84945913911&partnerID=8YFLogxK

U2 - 10.1039/c5cc05209b

DO - 10.1039/c5cc05209b

M3 - Article

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AN - SCOPUS:84945913911

SN - 1359-7345

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JO - CHEMICAL COMMUNICATIONS

JF - CHEMICAL COMMUNICATIONS

IS - 87

ER -

Dual metal and Lewis base catalysis approach for asymmetric synthesis of dihydroquinolines and the α-arylation of aldehydes via N-acyliminium ions

Abstract

Bibliographical note

ASJC Scopus subject areas

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