Substituted diarylmethylamines by stereospecific intramolecular electrophilic arylation of lithiated ureas

Jonathan Clayden; Jérémy Dufour; Damian M. Grainger; Madeleine Helliwell

doi:10.1021/ja071523a

Substituted diarylmethylamines by stereospecific intramolecular electrophilic arylation of lithiated ureas

Jonathan Clayden, Jérémy Dufour, Damian M. Grainger, Madeleine Helliwell

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

Abstract

On lithiation, N-benzyl ureas varying N′-aryl substituents undergo a migration of the aryl ring to the ∞ carbon of the N-benzyl group. With chiral, enantiomerically pure N-∞-methylbenzyl ureas, the rearrangement is stereospecific and creates a new, fully substituted stereogenic center ∞ to N. Removal of the urea function by N-nitrosation and hydrolysis allows the synthesis of chiral tertiary carbinamines in high enantiomeric purity. Copyright © 2007 American Chemical Society.

Original language	English
Pages (from-to)	7488-7489
Number of pages	1
Journal	Journal of the American Chemical Society
Volume	129
Issue number	24
DOIs	https://doi.org/10.1021/ja071523a
Publication status	Published - 20 Jun 2007

Keywords

TERT-BUTANESULFINYL KETIMINES
ASYMMETRIC-SYNTHESIS
CHIRAL AMINES
IMINES
REARRANGEMENTS
ALKYLATIONS
METALATION
REAGENTS

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title = "Substituted diarylmethylamines by stereospecific intramolecular electrophilic arylation of lithiated ureas",

abstract = "On lithiation, N-benzyl ureas varying N′-aryl substituents undergo a migration of the aryl ring to the ∞ carbon of the N-benzyl group. With chiral, enantiomerically pure N-∞-methylbenzyl ureas, the rearrangement is stereospecific and creates a new, fully substituted stereogenic center ∞ to N. Removal of the urea function by N-nitrosation and hydrolysis allows the synthesis of chiral tertiary carbinamines in high enantiomeric purity. Copyright {\textcopyright} 2007 American Chemical Society.",

keywords = "TERT-BUTANESULFINYL KETIMINES, ASYMMETRIC-SYNTHESIS, CHIRAL AMINES, IMINES, REARRANGEMENTS, ALKYLATIONS, METALATION, REAGENTS",

author = "Jonathan Clayden and J{\'e}r{\'e}my Dufour and Grainger, {Damian M.} and Madeleine Helliwell",

year = "2007",

month = jun,

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doi = "10.1021/ja071523a",

language = "English",

volume = "129",

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journal = "Journal of the American Chemical Society",

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TY - JOUR

T1 - Substituted diarylmethylamines by stereospecific intramolecular electrophilic arylation of lithiated ureas

AU - Clayden, Jonathan

AU - Dufour, Jérémy

AU - Grainger, Damian M.

AU - Helliwell, Madeleine

PY - 2007/6/20

Y1 - 2007/6/20

N2 - On lithiation, N-benzyl ureas varying N′-aryl substituents undergo a migration of the aryl ring to the ∞ carbon of the N-benzyl group. With chiral, enantiomerically pure N-∞-methylbenzyl ureas, the rearrangement is stereospecific and creates a new, fully substituted stereogenic center ∞ to N. Removal of the urea function by N-nitrosation and hydrolysis allows the synthesis of chiral tertiary carbinamines in high enantiomeric purity. Copyright © 2007 American Chemical Society.

AB - On lithiation, N-benzyl ureas varying N′-aryl substituents undergo a migration of the aryl ring to the ∞ carbon of the N-benzyl group. With chiral, enantiomerically pure N-∞-methylbenzyl ureas, the rearrangement is stereospecific and creates a new, fully substituted stereogenic center ∞ to N. Removal of the urea function by N-nitrosation and hydrolysis allows the synthesis of chiral tertiary carbinamines in high enantiomeric purity. Copyright © 2007 American Chemical Society.

KW - TERT-BUTANESULFINYL KETIMINES

KW - ASYMMETRIC-SYNTHESIS

KW - CHIRAL AMINES

KW - IMINES

KW - REARRANGEMENTS

KW - ALKYLATIONS

KW - METALATION

KW - REAGENTS

UR - https://www.ccdc.cam.ac.uk/structures/search?id=doi:10.5517/ccpy5xp&sid=DataCite

U2 - 10.1021/ja071523a

DO - 10.1021/ja071523a

M3 - Article

SN - 0002-7863

VL - 129

SP - 7488

EP - 7489

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 24

ER -

Substituted diarylmethylamines by stereospecific intramolecular electrophilic arylation of lithiated ureas

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Keywords

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