One-pot catalytic C-C double bond cleavage of α,β-enones aided by alkyl group-immobilized silica spheres

Dong Hun Lee; Eun Ae Jo; Jung Woo Park; Chul Ho Jun

doi:10.1016/j.tetlet.2009.10.103

One-pot catalytic C-C double bond cleavage of α,β-enones aided by alkyl group-immobilized silica spheres

Dong Hun Lee, Eun Ae Jo, Jung Woo Park, Chul Ho Jun

Department of Chemistry

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

16 Citations (Scopus)

Abstract

Catalytic C-C double bond cleavage of α,β-enones with a 1-alkene and H₂O was carried out in the presence of a (Ph₃P)₃RhCl catalyst, 2-amino-3-picoline, cyclohexylamine, benzoic acid, and alkyl group-immobilized silica spheres. Upon completion of the reaction, the corresponding ketones were obtained without needing a further hydrolysis step. In this reaction, alkyl group-immobilized silica spheres act as a water reservoir for hydrolysis of an intermediate ketimine and as a phase divider between the organic solution and H₂O.

Original language	English
Pages (from-to)	160-163
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2009.10.103
Publication status	Published - 2010 Jan 6

Bibliographical note

Funding Information:
This work was supported by a Korea Research Foundation Grant funded by the Korean Government (MOEHRD) ( KRF-2008-313-C00483 ), the WCU (World Class University) program through the Korea Science and Engineering Foundation funded by the Ministry of Education, Science and Technology ( R32-2008-000-10217-0 ) and the CBMH. D.H.L. and J.W.P. acknowledge the fellowships from the BK21 program of the Ministry of Education and Human Resources Development.

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "One-pot catalytic C-C double bond cleavage of α,β-enones aided by alkyl group-immobilized silica spheres",

abstract = "Catalytic C-C double bond cleavage of α,β-enones with a 1-alkene and H2O was carried out in the presence of a (Ph3P)3RhCl catalyst, 2-amino-3-picoline, cyclohexylamine, benzoic acid, and alkyl group-immobilized silica spheres. Upon completion of the reaction, the corresponding ketones were obtained without needing a further hydrolysis step. In this reaction, alkyl group-immobilized silica spheres act as a water reservoir for hydrolysis of an intermediate ketimine and as a phase divider between the organic solution and H2O.",

author = "Lee, {Dong Hun} and Jo, {Eun Ae} and Park, {Jung Woo} and Jun, {Chul Ho}",

note = "Funding Information: This work was supported by a Korea Research Foundation Grant funded by the Korean Government (MOEHRD) ( KRF-2008-313-C00483 ), the WCU (World Class University) program through the Korea Science and Engineering Foundation funded by the Ministry of Education, Science and Technology ( R32-2008-000-10217-0 ) and the CBMH. D.H.L. and J.W.P. acknowledge the fellowships from the BK21 program of the Ministry of Education and Human Resources Development.",

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AU - Lee, Dong Hun

AU - Jo, Eun Ae

AU - Park, Jung Woo

AU - Jun, Chul Ho

N1 - Funding Information: This work was supported by a Korea Research Foundation Grant funded by the Korean Government (MOEHRD) ( KRF-2008-313-C00483 ), the WCU (World Class University) program through the Korea Science and Engineering Foundation funded by the Ministry of Education, Science and Technology ( R32-2008-000-10217-0 ) and the CBMH. D.H.L. and J.W.P. acknowledge the fellowships from the BK21 program of the Ministry of Education and Human Resources Development.

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N2 - Catalytic C-C double bond cleavage of α,β-enones with a 1-alkene and H2O was carried out in the presence of a (Ph3P)3RhCl catalyst, 2-amino-3-picoline, cyclohexylamine, benzoic acid, and alkyl group-immobilized silica spheres. Upon completion of the reaction, the corresponding ketones were obtained without needing a further hydrolysis step. In this reaction, alkyl group-immobilized silica spheres act as a water reservoir for hydrolysis of an intermediate ketimine and as a phase divider between the organic solution and H2O.

AB - Catalytic C-C double bond cleavage of α,β-enones with a 1-alkene and H2O was carried out in the presence of a (Ph3P)3RhCl catalyst, 2-amino-3-picoline, cyclohexylamine, benzoic acid, and alkyl group-immobilized silica spheres. Upon completion of the reaction, the corresponding ketones were obtained without needing a further hydrolysis step. In this reaction, alkyl group-immobilized silica spheres act as a water reservoir for hydrolysis of an intermediate ketimine and as a phase divider between the organic solution and H2O.

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One-pot catalytic C-C double bond cleavage of α,β-enones aided by alkyl group-immobilized silica spheres

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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