Enantioselective Oxidative Coupling of Carboxylic Acids to α-Branched Aldehydes

Lars A. Leth; Line Næsborg; Gabriel J. Reyes-Rodríguez; Henriette N. Tobiesen; Marc V. Iversen; Karl Anker Jørgensen

doi:10.1021/jacs.8b07394

Enantioselective Oxidative Coupling of Carboxylic Acids to α-Branched Aldehydes

Lars A. Leth, Line Næsborg, Gabriel J. Reyes-Rodríguez, Henriette N. Tobiesen, Marc V. Iversen, Karl Anker Jørgensen^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

Abstract

A new reactivity in organocatalysis is proposed to account for the coupling of carboxylic acids to α-branched aldehydes by combining primary amine catalysis and an oxidant. The developed methodology is an enantioselective α-coupling of aromatic and aliphatic carboxylic acids to α-branched aldehydes and proceeds in high yields (up to 97%) and for most examples good enantioselectivities (up to 92% ee). On the basis of experimental and mechanistic observations, the role of the primary amine catalyst is discussed.

Original language	English
Journal	Journal of the American Chemical Society
Volume	140
Issue	40
Pages (from-to)	12687-12690
Number of pages	4
ISSN	0002-7863
DOIs	https://doi.org/10.1021/jacs.8b07394
Publication status	Published - 1 Jan 2018

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title = "Enantioselective Oxidative Coupling of Carboxylic Acids to α-Branched Aldehydes",

abstract = "A new reactivity in organocatalysis is proposed to account for the coupling of carboxylic acids to α-branched aldehydes by combining primary amine catalysis and an oxidant. The developed methodology is an enantioselective α-coupling of aromatic and aliphatic carboxylic acids to α-branched aldehydes and proceeds in high yields (up to 97%) and for most examples good enantioselectivities (up to 92% ee). On the basis of experimental and mechanistic observations, the role of the primary amine catalyst is discussed.",

author = "Leth, {Lars A.} and Line N{\ae}sborg and Reyes-Rodr{\'i}guez, {Gabriel J.} and Tobiesen, {Henriette N.} and Iversen, {Marc V.} and J{\o}rgensen, {Karl Anker}",

year = "2018",

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doi = "10.1021/jacs.8b07394",

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Enantioselective Oxidative Coupling of Carboxylic Acids to α-Branched Aldehydes. / Leth, Lars A.; Næsborg, Line; Reyes-Rodríguez, Gabriel J. et al.
In: Journal of the American Chemical Society, Vol. 140, No. 40, 01.01.2018, p. 12687-12690.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

TY - JOUR

T1 - Enantioselective Oxidative Coupling of Carboxylic Acids to α-Branched Aldehydes

AU - Leth, Lars A.

AU - Næsborg, Line

AU - Reyes-Rodríguez, Gabriel J.

AU - Tobiesen, Henriette N.

AU - Iversen, Marc V.

AU - Jørgensen, Karl Anker

PY - 2018/1/1

Y1 - 2018/1/1

N2 - A new reactivity in organocatalysis is proposed to account for the coupling of carboxylic acids to α-branched aldehydes by combining primary amine catalysis and an oxidant. The developed methodology is an enantioselective α-coupling of aromatic and aliphatic carboxylic acids to α-branched aldehydes and proceeds in high yields (up to 97%) and for most examples good enantioselectivities (up to 92% ee). On the basis of experimental and mechanistic observations, the role of the primary amine catalyst is discussed.

AB - A new reactivity in organocatalysis is proposed to account for the coupling of carboxylic acids to α-branched aldehydes by combining primary amine catalysis and an oxidant. The developed methodology is an enantioselective α-coupling of aromatic and aliphatic carboxylic acids to α-branched aldehydes and proceeds in high yields (up to 97%) and for most examples good enantioselectivities (up to 92% ee). On the basis of experimental and mechanistic observations, the role of the primary amine catalyst is discussed.

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U2 - 10.1021/jacs.8b07394

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AN - SCOPUS:85054277527

SN - 0002-7863

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SP - 12687

EP - 12690

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 40

ER -

Enantioselective Oxidative Coupling of Carboxylic Acids to α-Branched Aldehydes

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