Insertion of an Alkene into an ester: Intramolecular oxyacylation reaction of alkenes through acyl C-O bond activation

Giang T. Hoang; Venkata Jaganmohan Reddy; Huy H.K. Nguyen; Christopher J. Douglas

doi:10.1002/anie.201005767

Insertion of an Alkene into an ester: Intramolecular oxyacylation reaction of alkenes through acyl C-O bond activation

Giang T. Hoang
, Venkata Jaganmohan Reddy
, Huy H.K. Nguyen
, Christopher J. Douglas

Chemistry (Twin Cities)

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

37 Scopus citations

Abstract

Atom economy and esters: compatible now! The first catalytic insertion of a C-C bond into an acyl C-O bond was achieved using rhodium catalysts (see scheme). The products are β-alkoxy ketones with a fully substituted carbon center. Quinoline chelating groups were employed to stabilize the Rh-alkoxide intermediate.

Original language	English (US)
Pages (from-to)	1882-1884
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	8
DOIs	https://doi.org/10.1002/anie.201005767
State	Published - Feb 18 2011

Keywords

C-O activation
acylation
aldol reaction
homogeneous catalysis
rhodium

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10.1002/anie.201005767

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abstract = "Atom economy and esters: compatible now! The first catalytic insertion of a C-C bond into an acyl C-O bond was achieved using rhodium catalysts (see scheme). The products are β-alkoxy ketones with a fully substituted carbon center. Quinoline chelating groups were employed to stabilize the Rh-alkoxide intermediate.",

keywords = "C-O activation, acylation, aldol reaction, homogeneous catalysis, rhodium",

author = "Hoang, \{Giang T.\} and Reddy, \{Venkata Jaganmohan\} and Nguyen, \{Huy H.K.\} and Douglas, \{Christopher J.\}",

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AU - Reddy, Venkata Jaganmohan

AU - Nguyen, Huy H.K.

AU - Douglas, Christopher J.

PY - 2011/2/18

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N2 - Atom economy and esters: compatible now! The first catalytic insertion of a C-C bond into an acyl C-O bond was achieved using rhodium catalysts (see scheme). The products are β-alkoxy ketones with a fully substituted carbon center. Quinoline chelating groups were employed to stabilize the Rh-alkoxide intermediate.

AB - Atom economy and esters: compatible now! The first catalytic insertion of a C-C bond into an acyl C-O bond was achieved using rhodium catalysts (see scheme). The products are β-alkoxy ketones with a fully substituted carbon center. Quinoline chelating groups were employed to stabilize the Rh-alkoxide intermediate.

KW - C-O activation

KW - acylation

KW - aldol reaction

KW - homogeneous catalysis

KW - rhodium

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AN - SCOPUS:79951808168

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JO - Angewandte Chemie - International Edition

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IS - 8

ER -

Insertion of an Alkene into an ester: Intramolecular oxyacylation reaction of alkenes through acyl C-O bond activation

Abstract

Keywords

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