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

Research output: Contribution to journalArticle

13 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 languageEnglish
Pages (from-to)160-163
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number1
DOIs
Publication statusPublished - 2010 Jan 6

Fingerprint

Silicon Dioxide
Hydrolysis
Picolines
Cyclohexylamines
Benzoic Acid
Alkenes
Ketones
Catalysts
Water
ketimine
2-amino picoline

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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One-pot catalytic C-C double bond cleavage of α,β-enones aided by alkyl group-immobilized silica spheres. / Lee, Dong Hun; Jo, Eun Ae; Park, Jung Woo; Jun, Chul-Ho.

In: Tetrahedron Letters, Vol. 51, No. 1, 06.01.2010, p. 160-163.

Research output: Contribution to journalArticle

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T1 - One-pot catalytic C-C double bond cleavage of α,β-enones aided by alkyl group-immobilized silica spheres

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AU - Jo, Eun Ae

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AU - Jun, Chul-Ho

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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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