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

16 Citations (Scopus)

413 Downloads (Pure)

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

Research Groups and Themes

BCS and TECS CDTs
Organic & Biological

Access to Document

10.1021/acs.orglett.8b02468

Full-text PDF (accepted author manuscript)
This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at https://pubs.acs.org/doi/10.1021/acs.orglett.8b02468 . Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 936 KB

Handle.net

Persistent link

Cite this

@article{df059c204add41409c8f635c908e06a0,

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",

month = sep,

day = "21",

doi = "10.1021/acs.orglett.8b02468",

language = "English",

volume = "20",

pages = "5770--5773",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/85053496593

U2 - 10.1021/acs.orglett.8b02468

DO - 10.1021/acs.orglett.8b02468

M3 - Article (Academic Journal)

C2 - 30203980

AN - SCOPUS:85053496593

SN - 1523-7060

VL - 20

SP - 5770

EP - 5773

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

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

Abstract

Research Groups and Themes

Access to Document

Handle.net

Other files and links

Fingerprint

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

Cite this

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

Abstract

Research Groups and Themes

Access to Document

Handle.net

Other files and links

Fingerprint

Projects

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

Cite this