Dialkylation of indoles with trichloroacetimidates to access 3,3-disubstituted indolenines

Tamie Suzuki; Nilamber A. Mate; Arijit A. Adhikari; John D. Chisholm

doi:10.3390/molecules24224143

Dialkylation of indoles with trichloroacetimidates to access 3,3-disubstituted indolenines

Tamie Suzuki, Nilamber A. Mate, Arijit A. Adhikari, John D. Chisholm

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

3 Scopus citations

Abstract

2-Substituted indoles may be directly transformed to 3,3-dialkyl indolenines with trichloroacetimidate electrophiles and the Lewis acid TMSOTf. These reactions provide rapid access to complex indolenines which are present in a variety of complex natural products and medicinally relevant small molecule structures. This method provides an alternative to the use of transition metal catalysis. The indolenines are readily transformed into spiroindoline systems which are privileged scaffolds in medicinal chemistry.

Original language	English (US)
Article number	4143
Journal	Molecules
Volume	24
Issue number	22
DOIs	https://doi.org/10.3390/molecules24224143
State	Published - 2019

Keywords

Dialkylation
Indole
Indolenine
Spiroindoline
Trichloroacetimidate

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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10.3390/molecules24224143

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title = "Dialkylation of indoles with trichloroacetimidates to access 3,3-disubstituted indolenines",

abstract = "2-Substituted indoles may be directly transformed to 3,3-dialkyl indolenines with trichloroacetimidate electrophiles and the Lewis acid TMSOTf. These reactions provide rapid access to complex indolenines which are present in a variety of complex natural products and medicinally relevant small molecule structures. This method provides an alternative to the use of transition metal catalysis. The indolenines are readily transformed into spiroindoline systems which are privileged scaffolds in medicinal chemistry.",

keywords = "Dialkylation, Indole, Indolenine, Spiroindoline, Trichloroacetimidate",

author = "Tamie Suzuki and Mate, {Nilamber A.} and Adhikari, {Arijit A.} and Chisholm, {John D.}",

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year = "2019",

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language = "English (US)",

volume = "24",

journal = "Molecules",

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T1 - Dialkylation of indoles with trichloroacetimidates to access 3,3-disubstituted indolenines

AU - Suzuki, Tamie

AU - Mate, Nilamber A.

AU - Adhikari, Arijit A.

AU - Chisholm, John D.

PY - 2019

Y1 - 2019

N2 - 2-Substituted indoles may be directly transformed to 3,3-dialkyl indolenines with trichloroacetimidate electrophiles and the Lewis acid TMSOTf. These reactions provide rapid access to complex indolenines which are present in a variety of complex natural products and medicinally relevant small molecule structures. This method provides an alternative to the use of transition metal catalysis. The indolenines are readily transformed into spiroindoline systems which are privileged scaffolds in medicinal chemistry.

AB - 2-Substituted indoles may be directly transformed to 3,3-dialkyl indolenines with trichloroacetimidate electrophiles and the Lewis acid TMSOTf. These reactions provide rapid access to complex indolenines which are present in a variety of complex natural products and medicinally relevant small molecule structures. This method provides an alternative to the use of transition metal catalysis. The indolenines are readily transformed into spiroindoline systems which are privileged scaffolds in medicinal chemistry.

KW - Dialkylation

KW - Indole

KW - Indolenine

KW - Spiroindoline

KW - Trichloroacetimidate

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ER -

Dialkylation of indoles with trichloroacetimidates to access 3,3-disubstituted indolenines

Abstract

Keywords

ASJC Scopus subject areas

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