Direct β-activation of saturated aldehydes to formal michael acceptors through oxidative NHC catalysis

Junming Mo; Liang Shen; Yonggui Robin Chi

doi:10.1002/anie.201302152

Direct β-activation of saturated aldehydes to formal michael acceptors through oxidative NHC catalysis

Junming Mo, Liang Shen, Yonggui Robin Chi^*

^*Corresponding author for this work

Nanyang Technological University

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

139 Citations (Scopus)

Abstract

Without detours: Oxidative catalysis mediated by N-heterocyclic carbenes (NHCs) enables the direct β-carbon functionalization of saturated aldehydes (see scheme). The reaction proceeds through two sequential oxidative steps to generate α,β-unsaturated triazolium ester equivalents as formal Michael acceptors, which react with 1,3-diketones and β-ketone esters in an enantioselective manner.

Original language	English
Pages (from-to)	8588-8591
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	33
DOIs	https://doi.org/10.1002/anie.201302152
Publication status	Published - Aug 12 2013
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

β-activation
Michael addition
N-heterocyclic carbene
organocatalysis
synthetic methods

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10.1002/anie.201302152

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abstract = "Without detours: Oxidative catalysis mediated by N-heterocyclic carbenes (NHCs) enables the direct β-carbon functionalization of saturated aldehydes (see scheme). The reaction proceeds through two sequential oxidative steps to generate α,β-unsaturated triazolium ester equivalents as formal Michael acceptors, which react with 1,3-diketones and β-ketone esters in an enantioselective manner.",

keywords = "β-activation, Michael addition, N-heterocyclic carbene, organocatalysis, synthetic methods",

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Y1 - 2013/8/12

N2 - Without detours: Oxidative catalysis mediated by N-heterocyclic carbenes (NHCs) enables the direct β-carbon functionalization of saturated aldehydes (see scheme). The reaction proceeds through two sequential oxidative steps to generate α,β-unsaturated triazolium ester equivalents as formal Michael acceptors, which react with 1,3-diketones and β-ketone esters in an enantioselective manner.

AB - Without detours: Oxidative catalysis mediated by N-heterocyclic carbenes (NHCs) enables the direct β-carbon functionalization of saturated aldehydes (see scheme). The reaction proceeds through two sequential oxidative steps to generate α,β-unsaturated triazolium ester equivalents as formal Michael acceptors, which react with 1,3-diketones and β-ketone esters in an enantioselective manner.

KW - β-activation

KW - Michael addition

KW - N-heterocyclic carbene

KW - organocatalysis

KW - synthetic methods

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Direct β-activation of saturated aldehydes to formal michael acceptors through oxidative NHC catalysis

Abstract

ASJC Scopus Subject Areas

Keywords

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