The effects of amine and acid catalysts on efficient chelation-assisted hydroacylation of alkene with aliphatic aldehyde

Eun Ae Jo; Chul Ho Jun

doi:10.1016/j.tetlet.2009.02.091

The effects of amine and acid catalysts on efficient chelation-assisted hydroacylation of alkene with aliphatic aldehyde

Eun Ae Jo, Chul Ho Jun

Department of Chemistry

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

25 Citations (Scopus)

Abstract

Efficient intermolecular hydroacylation of 1-alkene with aliphatic aldehyde was achieved using a catalyst mixture of cyclohexylamine, p-trifluoromethylbenzoic acid, Wilkinson's complex and 2-amino-3-picoline. The formation of unwanted aldol side-product was avoided through the conjugate addition of cyclohexylamine to the aldol intermediate that was initially generated, followed by the retro-Mannich-type fragmentation of the resulting β-aminoaldimine.

Original language	English
Pages (from-to)	3338-3340
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2009.02.091
Publication status	Published - 2009 Jul 1

Bibliographical note

Funding Information:
This work was supported by the Korea Research Foundation Grant funded by the Korean Government (KRF-2008-313-C00483) and WCU (World Class University) programme through the Korea Science and Engineering Foundation funded by the Ministry of Education, Science and Technology (R32-2008-000-102170) and CBMH. E.-A.J. acknowledges the fellowships of the BK21 programme of the Ministry of Education and Human Resources Development.

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2009.02.091

Cite this

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abstract = "Efficient intermolecular hydroacylation of 1-alkene with aliphatic aldehyde was achieved using a catalyst mixture of cyclohexylamine, p-trifluoromethylbenzoic acid, Wilkinson's complex and 2-amino-3-picoline. The formation of unwanted aldol side-product was avoided through the conjugate addition of cyclohexylamine to the aldol intermediate that was initially generated, followed by the retro-Mannich-type fragmentation of the resulting β-aminoaldimine.",

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AB - Efficient intermolecular hydroacylation of 1-alkene with aliphatic aldehyde was achieved using a catalyst mixture of cyclohexylamine, p-trifluoromethylbenzoic acid, Wilkinson's complex and 2-amino-3-picoline. The formation of unwanted aldol side-product was avoided through the conjugate addition of cyclohexylamine to the aldol intermediate that was initially generated, followed by the retro-Mannich-type fragmentation of the resulting β-aminoaldimine.

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The effects of amine and acid catalysts on efficient chelation-assisted hydroacylation of alkene with aliphatic aldehyde

Abstract

Bibliographical note

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