Sequential double α-arylation of N -allylureas by asymmetric deprotonation and N→C aryl migration

Daniel J. Tetlow; Ulrich Hennecke; James Raftery; Michael J. Waring; David S. Clarke; Jonathan Clayden

doi:10.1021/ol102155h

Sequential double α-arylation of N -allylureas by asymmetric deprotonation and N→C aryl migration

Daniel J. Tetlow, Ulrich Hennecke, James Raftery, Michael J. Waring, David S. Clarke, Jonathan Clayden

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

Abstract

On lithiation with lithium amides, N-allyl-N'-aryl ureas undergo rearrangement with transfer of the aryl ring from N to the allylic α carbon. From the α-arylated products, a further aryl transfer under the influence of a chiral lithium amide allows the enantioselective construction of 1,1-diarylallylamine derivatives. Stereoselectivity in these reactions results from the enantioselective formation of a planar chiral allyllithium under kinetic control. © 2010 American Chemical Society.

Original language	English
Pages (from-to)	5442-5445
Number of pages	3
Journal	Organic Letters
Volume	12
Issue number	23
DOIs	https://doi.org/10.1021/ol102155h
Publication status	Published - 3 Dec 2010

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10.1021/ol102155h

CCDC 777622: Experimental Crystal Structure Determination
Tetlow, D. J. (Contributor), Hennecke, U. (Contributor), Raftery, J. (Contributor), Waring, M. J. (Contributor), Clarke, D. S. (Contributor) & Clayden, J. (Contributor), Cambridge Crystallographic Data Centre, 2010
DOI: 10.5517/ccv35lp, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccv35lp&sid=DataCite
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title = "Sequential double α-arylation of N -allylureas by asymmetric deprotonation and N→C aryl migration",

abstract = "On lithiation with lithium amides, N-allyl-N'-aryl ureas undergo rearrangement with transfer of the aryl ring from N to the allylic α carbon. From the α-arylated products, a further aryl transfer under the influence of a chiral lithium amide allows the enantioselective construction of 1,1-diarylallylamine derivatives. Stereoselectivity in these reactions results from the enantioselective formation of a planar chiral allyllithium under kinetic control. {\textcopyright} 2010 American Chemical Society.",

author = "Tetlow, {Daniel J.} and Ulrich Hennecke and James Raftery and Waring, {Michael J.} and Clarke, {David S.} and Jonathan Clayden",

year = "2010",

month = dec,

day = "3",

doi = "10.1021/ol102155h",

language = "English",

volume = "12",

pages = "5442--5445",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Sequential double α-arylation of N -allylureas by asymmetric deprotonation and N→C aryl migration

AU - Tetlow, Daniel J.

AU - Hennecke, Ulrich

AU - Raftery, James

AU - Waring, Michael J.

AU - Clarke, David S.

AU - Clayden, Jonathan

PY - 2010/12/3

Y1 - 2010/12/3

N2 - On lithiation with lithium amides, N-allyl-N'-aryl ureas undergo rearrangement with transfer of the aryl ring from N to the allylic α carbon. From the α-arylated products, a further aryl transfer under the influence of a chiral lithium amide allows the enantioselective construction of 1,1-diarylallylamine derivatives. Stereoselectivity in these reactions results from the enantioselective formation of a planar chiral allyllithium under kinetic control. © 2010 American Chemical Society.

AB - On lithiation with lithium amides, N-allyl-N'-aryl ureas undergo rearrangement with transfer of the aryl ring from N to the allylic α carbon. From the α-arylated products, a further aryl transfer under the influence of a chiral lithium amide allows the enantioselective construction of 1,1-diarylallylamine derivatives. Stereoselectivity in these reactions results from the enantioselective formation of a planar chiral allyllithium under kinetic control. © 2010 American Chemical Society.

U2 - 10.1021/ol102155h

DO - 10.1021/ol102155h

M3 - Article

SN - 1523-7052

VL - 12

SP - 5442

EP - 5445

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Sequential double α-arylation of N -allylureas by asymmetric deprotonation and N→C aryl migration

Abstract

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CCDC 777622: Experimental Crystal Structure Determination

Cite this