Polycyclic Indoline Derivatives by Dearomatizing Anionic Cyclization of Indole and Tryptamine-Derived Ureas

Jessica E. Hill; Quentin Lefebvre; Laura A. Fraser; Jonathan Clayden

doi:10.1021/acs.orglett.8b02468

Polycyclic Indoline Derivatives by Dearomatizing Anionic Cyclization of Indole and Tryptamine-Derived Ureas

Jessica E. Hill, Quentin Lefebvre, Laura A. Fraser, Jonathan Clayden^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

The base-promoted dearomatizing cyclization of anionic indole-containing urea derivatives provided tri- or tetracyclic indoline-containing scaffolds from lithiated urea intermediates. 3-Substituted indoles, including tryptamine derivatives, generally underwent the reaction in high yield and with excellent diastereoselectivity. In situ IR spectroscopy suggests a deprotonation-carbolithiation-reprotonation mechanism.

Original language	English
Pages (from-to)	5770-5773
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	18
Early online date	11 Sept 2018
DOIs	https://doi.org/10.1021/acs.orglett.8b02468
Publication status	Published - 21 Sept 2018

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title = "Polycyclic Indoline Derivatives by Dearomatizing Anionic Cyclization of Indole and Tryptamine-Derived Ureas",

abstract = "The base-promoted dearomatizing cyclization of anionic indole-containing urea derivatives provided tri- or tetracyclic indoline-containing scaffolds from lithiated urea intermediates. 3-Substituted indoles, including tryptamine derivatives, generally underwent the reaction in high yield and with excellent diastereoselectivity. In situ IR spectroscopy suggests a deprotonation-carbolithiation-reprotonation mechanism.",

author = "Hill, {Jessica E.} and Quentin Lefebvre and Fraser, {Laura A.} and Jonathan Clayden",

year = "2018",

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T1 - Polycyclic Indoline Derivatives by Dearomatizing Anionic Cyclization of Indole and Tryptamine-Derived Ureas

AU - Hill, Jessica E.

AU - Lefebvre, Quentin

AU - Fraser, Laura A.

AU - Clayden, Jonathan

PY - 2018/9/21

Y1 - 2018/9/21

N2 - The base-promoted dearomatizing cyclization of anionic indole-containing urea derivatives provided tri- or tetracyclic indoline-containing scaffolds from lithiated urea intermediates. 3-Substituted indoles, including tryptamine derivatives, generally underwent the reaction in high yield and with excellent diastereoselectivity. In situ IR spectroscopy suggests a deprotonation-carbolithiation-reprotonation mechanism.

AB - The base-promoted dearomatizing cyclization of anionic indole-containing urea derivatives provided tri- or tetracyclic indoline-containing scaffolds from lithiated urea intermediates. 3-Substituted indoles, including tryptamine derivatives, generally underwent the reaction in high yield and with excellent diastereoselectivity. In situ IR spectroscopy suggests a deprotonation-carbolithiation-reprotonation mechanism.

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DO - 10.1021/acs.orglett.8b02468

M3 - Article (Academic Journal)

C2 - 30203980

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Polycyclic Indoline Derivatives by Dearomatizing Anionic Cyclization of Indole and Tryptamine-Derived Ureas

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alpha-Arylation and alpha-Vinylation of Enolates: New Reactivity from the Urea Linkage.

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Polycyclic Indoline Derivatives by Dearomatizing Anionic Cyclization of Indole and Tryptamine-Derived Ureas

Abstract

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alpha-Arylation and alpha-Vinylation of Enolates: New Reactivity from the Urea Linkage.

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