New Initiation Modes for Directed Carbonylative C-C Bond Activation: Rhodium-Catalyzed (3+1+2) Cycloadditions of Aminomethylcyclopropanes

Gangwei Wang; Niall McCreanor; Megan Shaw; William G. Whittingham; John Bower

doi:10.1021/jacs.6b08608

New Initiation Modes for Directed Carbonylative C-C Bond Activation: Rhodium-Catalyzed (3+1+2) Cycloadditions of Aminomethylcyclopropanes

Gangwei Wang, Niall McCreanor, Megan Shaw, William G. Whittingham, John Bower

School of Chemistry

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

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Abstract

Under carbonylative conditions, neutral Rh(I)-systems modified with weak donor ligands (AsPh₃ or 1,4-oxathiane) undergo N-Cbz, N-benzoyl or N-Ts directed insertion into the proximal C-C bond of aminomethylcyclopropanes to generate rhodacyclopentanone intermediates. These are trapped by N-tethered alkenes to provide complex perhydroisoindoles.

Original language	English
Pages (from-to)	13501-13504
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	41
Early online date	6 Oct 2016
DOIs	https://doi.org/10.1021/jacs.6b08608
Publication status	Published - 19 Oct 2016

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This is the final published version of the article (version of record). It first appeared online via ACS at http://pubs.acs.org/doi/abs/10.1021/jacs.6b08608. Please refer to any applicable terms of use of the publisher.
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This is the final published version of the article (version of record). It first appeared online via ACS at http://pubs.acs.org/doi/abs/10.1021/jacs.6b08608. Please refer to any applicable terms of use of the publisher.
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A 13C NMR Coldprobe to Underpin Chemistry Research.
Butts, C. P. (Principal Investigator)
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@article{d57c2884adef432d894c1c8a82b23ab4,

title = "New Initiation Modes for Directed Carbonylative C-C Bond Activation: Rhodium-Catalyzed (3+1+2) Cycloadditions of Aminomethylcyclopropanes",

abstract = "Under carbonylative conditions, neutral Rh(I)-systems modified with weak donor ligands (AsPh3 or 1,4-oxathiane) undergo N-Cbz, N-benzoyl or N-Ts directed insertion into the proximal C-C bond of aminomethylcyclopropanes to generate rhodacyclopentanone intermediates. These are trapped by N-tethered alkenes to provide complex perhydroisoindoles.",

author = "Gangwei Wang and Niall McCreanor and Megan Shaw and Whittingham, \{William G.\} and John Bower",

year = "2016",

month = oct,

day = "19",

doi = "10.1021/jacs.6b08608",

language = "English",

volume = "138",

pages = "13501--13504",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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New Initiation Modes for Directed Carbonylative C-C Bond Activation: Rhodium-Catalyzed (3+1+2) Cycloadditions of Aminomethylcyclopropanes. / Wang, Gangwei; McCreanor, Niall; Shaw, Megan et al.
In: Journal of the American Chemical Society, Vol. 138, No. 41, 19.10.2016, p. 13501-13504.

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

TY - JOUR

T1 - New Initiation Modes for Directed Carbonylative C-C Bond Activation

T2 - Rhodium-Catalyzed (3+1+2) Cycloadditions of Aminomethylcyclopropanes

AU - Wang, Gangwei

AU - McCreanor, Niall

AU - Shaw, Megan

AU - Whittingham, William G.

AU - Bower, John

PY - 2016/10/19

Y1 - 2016/10/19

N2 - Under carbonylative conditions, neutral Rh(I)-systems modified with weak donor ligands (AsPh3 or 1,4-oxathiane) undergo N-Cbz, N-benzoyl or N-Ts directed insertion into the proximal C-C bond of aminomethylcyclopropanes to generate rhodacyclopentanone intermediates. These are trapped by N-tethered alkenes to provide complex perhydroisoindoles.

AB - Under carbonylative conditions, neutral Rh(I)-systems modified with weak donor ligands (AsPh3 or 1,4-oxathiane) undergo N-Cbz, N-benzoyl or N-Ts directed insertion into the proximal C-C bond of aminomethylcyclopropanes to generate rhodacyclopentanone intermediates. These are trapped by N-tethered alkenes to provide complex perhydroisoindoles.

U2 - 10.1021/jacs.6b08608

DO - 10.1021/jacs.6b08608

M3 - Article (Academic Journal)

C2 - 27709913

SN - 0002-7863

VL - 138

SP - 13501

EP - 13504

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 41

ER -

New Initiation Modes for Directed Carbonylative C-C Bond Activation: Rhodium-Catalyzed (3+1+2) Cycloadditions of Aminomethylcyclopropanes

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