Gold-catalyzed tandem C-C and C-O bond formation: A highly diastereoselective formation of cyclohex-4-ene-1,2-diol derivatives

Choongmin Lim, Ji Eun Kang, Ji Eun Lee, Seunghoon Shin

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

We have reported an efficient gold(I)-catalyzed tandem cyclization of (erf-butyl carbonate derivatives of hex-1-en-5-yn-3-ol where nucleophilic participation of the O-Boc group appears to intercept a carbocationic (or cyclopropyl carbene) Au intermediate. This novel protocol leads to densely functionalized cyclohexene-3,4-diol derivatives where 1,2- or 1,2,3-stereocenters are controlled in a highly diastereoselective fashion.

Original languageEnglish
Pages (from-to)3539-3542
Number of pages4
JournalOrganic Letters
Volume9
Issue number18
DOIs
StatePublished - 2007 Aug 30

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Carbonates
carbenes
Cyclization
Gold
carbonates
gold
Derivatives
cyclohexene
carbene

Cite this

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abstract = "We have reported an efficient gold(I)-catalyzed tandem cyclization of (erf-butyl carbonate derivatives of hex-1-en-5-yn-3-ol where nucleophilic participation of the O-Boc group appears to intercept a carbocationic (or cyclopropyl carbene) Au intermediate. This novel protocol leads to densely functionalized cyclohexene-3,4-diol derivatives where 1,2- or 1,2,3-stereocenters are controlled in a highly diastereoselective fashion.",
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Gold-catalyzed tandem C-C and C-O bond formation : A highly diastereoselective formation of cyclohex-4-ene-1,2-diol derivatives. / Lim, Choongmin; Kang, Ji Eun; Lee, Ji Eun; Shin, Seunghoon.

In: Organic Letters, Vol. 9, No. 18, 30.08.2007, p. 3539-3542.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Gold-catalyzed tandem C-C and C-O bond formation

T2 - A highly diastereoselective formation of cyclohex-4-ene-1,2-diol derivatives

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AU - Kang, Ji Eun

AU - Lee, Ji Eun

AU - Shin, Seunghoon

PY - 2007/8/30

Y1 - 2007/8/30

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