Application of Rh(l)-Catalyzed C - H Bond Activation to the Ring Opening of 2-Cycloalkenones in the Presence of Amines

Chul Ho Jun, Choong Woon Moon, Sung Gon Lim, Hyuk Lee

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

(matrix presented) Herein described is the application of the Rh(l)-catalyzed C-H bond activation to the ring-opening of 2-cycloalkenones in the presence of cyclohexylamine. This reaction includes the C-C double bond cleavage of 2-cycloalkenones through the conjugate addition of cyclohexylamine followed by the retro-Mannich-type fragmentation. The resulting ring-opened intermediates subsequently underwent either chelation-assisted hydroacylation to afford a ring-opened dicarbonyl compound or β-alkylation via a ring contraction.

Original languageEnglish
Pages (from-to)1595-1597
Number of pages3
JournalOrganic Letters
Volume4
Issue number9
DOIs
Publication statusPublished - 2002 May 2

Fingerprint

Cyclohexylamines
Amines
amines
Chemical activation
activation
rings
Alkylation
Chelation
chelation
alkylation
contraction
cleavage
fragmentation
matrices

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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Application of Rh(l)-Catalyzed C - H Bond Activation to the Ring Opening of 2-Cycloalkenones in the Presence of Amines. / Jun, Chul Ho; Moon, Choong Woon; Lim, Sung Gon; Lee, Hyuk.

In: Organic Letters, Vol. 4, No. 9, 02.05.2002, p. 1595-1597.

Research output: Contribution to journalArticle

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