Synthesis of 1-arylcycloalkenamines by intramolecular arylation of lithiated ureas

Michael B. Tait; Philipp A. Ottersbach; Daniel J. Tetlow; Jonathan Clayden

doi:10.1021/op500173q

Synthesis of 1-arylcycloalkenamines by intramolecular arylation of lithiated ureas

Michael B. Tait
, Philipp A. Ottersbach
, Daniel J. Tetlow
, Jonathan Clayden^*

^*Corresponding author for this work

School of Chemistry

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

9 Citations (Scopus)

Abstract

The deprotonation of N′-arylurea derivatives of cyclohexenamines by alkyllithiums leads to migration of the N′-aryl substituent from N′ to the allylic position α to N via rearrangement of a urea-stabilised allyllithium intermediate. The product ureas may be solvolysed to reveal 1-arylcyclohexenamines.

Original language	English
Pages (from-to)	1245-1252
Number of pages	8
Journal	Organic Process Research & Development
Volume	18
Issue number	10
Early online date	21 Jul 2014
DOIs	https://doi.org/10.1021/op500173q
Publication status	Published - 17 Oct 2014

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Organic & Biological

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title = "Synthesis of 1-arylcycloalkenamines by intramolecular arylation of lithiated ureas",

abstract = "The deprotonation of N′-arylurea derivatives of cyclohexenamines by alkyllithiums leads to migration of the N′-aryl substituent from N′ to the allylic position α to N via rearrangement of a urea-stabilised allyllithium intermediate. The product ureas may be solvolysed to reveal 1-arylcyclohexenamines.",

author = "Tait, \{Michael B.\} and Ottersbach, \{Philipp A.\} and Tetlow, \{Daniel J.\} and Jonathan Clayden",

year = "2014",

month = oct,

day = "17",

doi = "10.1021/op500173q",

language = "English",

volume = "18",

pages = "1245--1252",

journal = "Organic Process Research \& Development",

issn = "1083-6160",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - Synthesis of 1-arylcycloalkenamines by intramolecular arylation of lithiated ureas

AU - Tait, Michael B.

AU - Ottersbach, Philipp A.

AU - Tetlow, Daniel J.

AU - Clayden, Jonathan

PY - 2014/10/17

Y1 - 2014/10/17

N2 - The deprotonation of N′-arylurea derivatives of cyclohexenamines by alkyllithiums leads to migration of the N′-aryl substituent from N′ to the allylic position α to N via rearrangement of a urea-stabilised allyllithium intermediate. The product ureas may be solvolysed to reveal 1-arylcyclohexenamines.

AB - The deprotonation of N′-arylurea derivatives of cyclohexenamines by alkyllithiums leads to migration of the N′-aryl substituent from N′ to the allylic position α to N via rearrangement of a urea-stabilised allyllithium intermediate. The product ureas may be solvolysed to reveal 1-arylcyclohexenamines.

UR - https://www.scopus.com/pages/publications/84908066292

U2 - 10.1021/op500173q

DO - 10.1021/op500173q

M3 - Article (Academic Journal)

AN - SCOPUS:84908066292

SN - 1083-6160

VL - 18

SP - 1245

EP - 1252

JO - Organic Process Research & Development

JF - Organic Process Research & Development

IS - 10

ER -

Synthesis of 1-arylcycloalkenamines by intramolecular arylation of lithiated ureas

Abstract

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

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Synthesis of 1-arylcycloalkenamines by intramolecular arylation of lithiated ureas

Abstract

Research Groups and Themes

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

Cite this