Directing group enhanced carbonylative ring expansions of amino-substituted cyclopropanes: rhodium-catalyzed multicomponent synthesis of N-heterobicyclic enones

Megan H. Shaw; Ekaterina Y. Melikhova; Daniel P. Kloer; William G. Whittingham; John F. Bower

doi:10.1021/ja401936c

Directing group enhanced carbonylative ring expansions of amino-substituted cyclopropanes: rhodium-catalyzed multicomponent synthesis of N-heterobicyclic enones

Megan H. Shaw
, Ekaterina Y. Melikhova
, Daniel P. Kloer
, William G. Whittingham
, John F. Bower^*

^*Corresponding author for this work

School of Chemistry

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

114 Citations (Scopus)

Abstract

Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C-C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a blueprint for myriad N-heterocyclic methodologies.

Original language	English
Pages (from-to)	4992-4995
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	13
DOIs	https://doi.org/10.1021/ja401936c
Publication status	Published - 2 Apr 2013

Research Groups and Themes

BCS and TECS CDTs

Keywords

C-C BOND
CARBON-CARBON
ORGANIC-SYNTHESIS
ORGANOMETALLIC CHEMISTRY
CYCLOADDITION REACTION
ATOM ECONOMY
ACTIVATION
INSERTION
METALS
CARBOCYCLIZATION

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http://pubs.acs.org/doi/abs/10.1021/ja401936c

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@article{4bc471968f74424aa4fc542a7915722f,

title = "Directing group enhanced carbonylative ring expansions of amino-substituted cyclopropanes: rhodium-catalyzed multicomponent synthesis of N-heterobicyclic enones",

abstract = "Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C-C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a blueprint for myriad N-heterocyclic methodologies.",

keywords = "C-C BOND, CARBON-CARBON, ORGANIC-SYNTHESIS, ORGANOMETALLIC CHEMISTRY, CYCLOADDITION REACTION, ATOM ECONOMY, ACTIVATION, INSERTION, METALS, CARBOCYCLIZATION",

author = "Shaw, \{Megan H.\} and Melikhova, \{Ekaterina Y.\} and Kloer, \{Daniel P.\} and Whittingham, \{William G.\} and Bower, \{John F.\}",

year = "2013",

month = apr,

day = "2",

doi = "10.1021/ja401936c",

language = "English",

volume = "135",

pages = "4992--4995",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "13",

}

Directing group enhanced carbonylative ring expansions of amino-substituted cyclopropanes: rhodium-catalyzed multicomponent synthesis of N-heterobicyclic enones. / Shaw, Megan H.; Melikhova, Ekaterina Y.; Kloer, Daniel P. et al.
In: Journal of the American Chemical Society, Vol. 135, No. 13, 02.04.2013, p. 4992-4995.

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

TY - JOUR

T1 - Directing group enhanced carbonylative ring expansions of amino-substituted cyclopropanes: rhodium-catalyzed multicomponent synthesis of N-heterobicyclic enones

AU - Shaw, Megan H.

AU - Melikhova, Ekaterina Y.

AU - Kloer, Daniel P.

AU - Whittingham, William G.

AU - Bower, John F.

PY - 2013/4/2

Y1 - 2013/4/2

N2 - Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C-C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a blueprint for myriad N-heterocyclic methodologies.

AB - Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C-C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a blueprint for myriad N-heterocyclic methodologies.

KW - C-C BOND

KW - CARBON-CARBON

KW - ORGANIC-SYNTHESIS

KW - ORGANOMETALLIC CHEMISTRY

KW - CYCLOADDITION REACTION

KW - ATOM ECONOMY

KW - ACTIVATION

KW - INSERTION

KW - METALS

KW - CARBOCYCLIZATION

UR - https://www.scopus.com/pages/publications/84875772642

U2 - 10.1021/ja401936c

DO - 10.1021/ja401936c

M3 - Article (Academic Journal)

C2 - 23488745

SN - 0002-7863

VL - 135

SP - 4992

EP - 4995

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 13

ER -

Directing group enhanced carbonylative ring expansions of amino-substituted cyclopropanes: rhodium-catalyzed multicomponent synthesis of N-heterobicyclic enones

Abstract

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Directing group enhanced carbonylative ring expansions of amino-substituted cyclopropanes: rhodium-catalyzed multicomponent synthesis of N-heterobicyclic enones

Abstract

Research Groups and Themes

Keywords

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3-month Core Capability for Chemistry Research

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