Journal of the American Chemical Society, volume 137, issue 1, pages 463-468
Reversible C–C Bond Activation Enables Stereocontrol in Rh-Catalyzed Carbonylative Cycloadditions of Aminocyclopropanes
2
Syngenta, Jealott’s Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, United Kingdom
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Publication type: Journal Article
Publication date: 2014-12-24
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Upon exposure to neutral or cationic Rh(I)-catalyst systems, amino-substituted cyclopropanes undergo carbonylative cycloaddition with tethered alkenes to provide stereochemically complex N-heterocyclic scaffolds. These processes rely upon the generation and trapping of rhodacyclopentanone intermediates, which arise by regioselective, Cbz-directed insertion of Rh and CO into one of the two proximal aminocyclopropane C–C bonds. For cyclizations using cationic Rh(I)-systems, synthetic and mechanistic studies indicate that rhodacyclopentanone formation is reversible and that the alkene insertion step determines product diastereoselectivity. This regime facilitates high levels of stereocontrol with respect to substituents on the alkene tether. The option of generating rhodacyclopentanones dynamically provides a new facet to a growing area of catalysis and may find use as a (stereo)control strategy in other processes.
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5
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1 publication, 1.22%
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5
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25
30
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Shaw M. H. et al. Reversible C–C Bond Activation Enables Stereocontrol in Rh-Catalyzed Carbonylative Cycloadditions of Aminocyclopropanes // Journal of the American Chemical Society. 2014. Vol. 137. No. 1. pp. 463-468.
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Shaw M. H., Mccreanor N. G., Whittingham W. G., Bower J. E. Reversible C–C Bond Activation Enables Stereocontrol in Rh-Catalyzed Carbonylative Cycloadditions of Aminocyclopropanes // Journal of the American Chemical Society. 2014. Vol. 137. No. 1. pp. 463-468.
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TY - JOUR
DO - 10.1021/ja511335v
UR - https://doi.org/10.1021/ja511335v
TI - Reversible C–C Bond Activation Enables Stereocontrol in Rh-Catalyzed Carbonylative Cycloadditions of Aminocyclopropanes
T2 - Journal of the American Chemical Society
AU - Shaw, Megan H
AU - Mccreanor, Niall G
AU - Whittingham, William G
AU - Bower, John Eric
PY - 2014
DA - 2014/12/24 00:00:00
PB - American Chemical Society (ACS)
SP - 463-468
IS - 1
VL - 137
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2014_Shaw,
author = {Megan H Shaw and Niall G Mccreanor and William G Whittingham and John Eric Bower},
title = {Reversible C–C Bond Activation Enables Stereocontrol in Rh-Catalyzed Carbonylative Cycloadditions of Aminocyclopropanes},
journal = {Journal of the American Chemical Society},
year = {2014},
volume = {137},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/ja511335v},
number = {1},
pages = {463--468},
doi = {10.1021/ja511335v}
}
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MLA
Copy
Shaw, Megan H., et al. “Reversible C–C Bond Activation Enables Stereocontrol in Rh-Catalyzed Carbonylative Cycloadditions of Aminocyclopropanes.” Journal of the American Chemical Society, vol. 137, no. 1, Dec. 2014, pp. 463-468. https://doi.org/10.1021/ja511335v.