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

NomaanM. Rezayee; Vibeke H. Lauridsen; Line Naesborg; Thanh V. Q. Nguyen; Henriette N. Tobiesen; Karl Anker Jorgensen

doi:10.1039/c9sc00196d

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

NomaanM. Rezayee, Vibeke H. Lauridsen, Line Naesborg, Thanh V. Q. Nguyen, Henriette N. Tobiesen, Karl Anker Jorgensen^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

Abstract

The first organocatalysed, metal-free cross-nucleophile coupling of indoles with α-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 α-branched aldehydes.

Original language	English
Journal	Chemical Science
Volume	10
Issue	12
Pages (from-to)	3586-3591
Number of pages	6
ISSN	2041-6520
DOIs	https://doi.org/10.1039/c9sc00196d
Publication status	Published - Mar 2019

Keywords

ALPHA-ARYLATION
ALKYLATION
AMINES

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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 α-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 α-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",

}

Oxidative organocatalysed enantioselective coupling of indoles with aldehydes that forms quaternary carbon stereocentres. / Rezayee, NomaanM.; Lauridsen, Vibeke H.; Naesborg, Line et al.
In: Chemical Science, Vol. 10, No. 12, 03.2019, p. 3586-3591.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

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 α-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 α-branched aldehydes.

AB - The first organocatalysed, metal-free cross-nucleophile coupling of indoles with α-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 α-branched aldehydes.

KW - ALPHA-ARYLATION

KW - ALKYLATION

KW - AMINES

UR - http://www.scopus.com/inward/record.url?scp=85063356873&partnerID=8YFLogxK

U2 - 10.1039/c9sc00196d

DO - 10.1039/c9sc00196d

M3 - Journal article

C2 - 30996950

SN - 2041-6520

VL - 10

SP - 3586

EP - 3591

JO - Chemical Science

JF - Chemical Science

IS - 12

ER -

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

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Keywords

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