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Karl Anker Jørgensen

Oxidative organocatalysed enantioselective coupling of indoles with aldehydes that forms quaternary carbon stereocentres

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Oxidative organocatalysed enantioselective coupling of indoles with aldehydes that forms quaternary carbon stereocentres. / Rezayee, NomaanM.; Lauridsen, Vibeke H.; Naesborg, Line; Nguyen, Thanh V. Q.; Tobiesen, Henriette N.; Jorgensen, Karl Anker.

In: Chemical Science, Vol. 10, No. 12, 03.2019, p. 3586-3591.

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@article{f551df6b70934a1384753d139e92f922,
title = "Oxidative organocatalysed enantioselective coupling of indoles with aldehydes that forms quaternary carbon stereocentres",
abstract = "The first organocatalysed, metal-free cross-nucleophile coupling of indoles with -branched aldehydes forming acyclic stereoselective quaternary carbon centres is presented. Applying an amino acid-derived catalyst with suitable organic oxidants affords the desired enantioenriched indole functionalised products with moderate to excellent yield and enantioselectivity. Two metal-free oxidative protocols employing either DDQ or a sequential approach that uses two organocatalysts to facilitate the use of O-2 as the terminal oxidant are disclosed. These methods are compatible with various indoles ranging from electron-rich to -deficient substituents at the C-2, -5, -6, and -7-positions reacting with a series of different -branched aldehydes.",
keywords = "ALPHA-ARYLATION, ALKYLATION, AMINES",
author = "NomaanM. Rezayee and Lauridsen, {Vibeke H.} and Line Naesborg and Nguyen, {Thanh V. Q.} and Tobiesen, {Henriette N.} and Jorgensen, {Karl Anker}",
year = "2019",
month = mar,
doi = "10.1039/c9sc00196d",
language = "English",
volume = "10",
pages = "3586--3591",
journal = "Chemical Science",
issn = "2041-6520",
publisher = "royal society of chemistry",
number = "12",

}

RIS

TY - JOUR

T1 - Oxidative organocatalysed enantioselective coupling of indoles with aldehydes that forms quaternary carbon stereocentres

AU - Rezayee, NomaanM.

AU - Lauridsen, Vibeke H.

AU - Naesborg, Line

AU - Nguyen, Thanh V. Q.

AU - Tobiesen, Henriette N.

AU - Jorgensen, Karl Anker

PY - 2019/3

Y1 - 2019/3

N2 - The first organocatalysed, metal-free cross-nucleophile coupling of indoles with -branched aldehydes forming acyclic stereoselective quaternary carbon centres is presented. Applying an amino acid-derived catalyst with suitable organic oxidants affords the desired enantioenriched indole functionalised products with moderate to excellent yield and enantioselectivity. Two metal-free oxidative protocols employing either DDQ or a sequential approach that uses two organocatalysts to facilitate the use of O-2 as the terminal oxidant are disclosed. These methods are compatible with various indoles ranging from electron-rich to -deficient substituents at the C-2, -5, -6, and -7-positions reacting with a series of different -branched aldehydes.

AB - The first organocatalysed, metal-free cross-nucleophile coupling of indoles with -branched aldehydes forming acyclic stereoselective quaternary carbon centres is presented. Applying an amino acid-derived catalyst with suitable organic oxidants affords the desired enantioenriched indole functionalised products with moderate to excellent yield and enantioselectivity. Two metal-free oxidative protocols employing either DDQ or a sequential approach that uses two organocatalysts to facilitate the use of O-2 as the terminal oxidant are disclosed. These methods are compatible with various indoles ranging from electron-rich to -deficient substituents at the C-2, -5, -6, and -7-positions reacting with a series of different -branched aldehydes.

KW - ALPHA-ARYLATION

KW - ALKYLATION

KW - AMINES

U2 - 10.1039/c9sc00196d

DO - 10.1039/c9sc00196d

M3 - Journal article

C2 - 30996950

VL - 10

SP - 3586

EP - 3591

JO - Chemical Science

JF - Chemical Science

SN - 2041-6520

IS - 12

ER -