Diastereoselective manipulations of bicyclo[m.1.0] alkane derivatives. 3. Nucleophilic additions to the carbonyl carbon of (1R,8R)-Bicyclo[6.1.0]nonan-2,6-dione 2-(2S,3S)-1,4-Di-O-methyl-1,2,3,4-butane ketal

Eugene A Mash, Kalpana S. Nimkar, James A. Baron

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Conformations of the title compound were studied using a Monte Carlo search technique. Two principal conformational motifs were observed for the bicyclic carbocycle in which both faces of the carbonyl appear susceptible to nucleophilic attack. The title compound was synthesized in eight steps from cis-1,5-cyclooctanediol. Additions of nucleophiles (e.g., CH3Li) to the title compound gave adducts in good yields, but with low levels of diastereoselectivity, in agreement with computational prediction.

Original languageEnglish (US)
Pages (from-to)9043-9056
Number of pages14
JournalTetrahedron
Volume53
Issue number27
DOIs
StatePublished - Jul 7 1997

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Nucleophiles
Alkanes
Conformations
Carbon
Derivatives
butane

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "Diastereoselective manipulations of bicyclo[m.1.0] alkane derivatives. 3. Nucleophilic additions to the carbonyl carbon of (1R,8R)-Bicyclo[6.1.0]nonan-2,6-dione 2-(2S,3S)-1,4-Di-O-methyl-1,2,3,4-butane ketal",
abstract = "Conformations of the title compound were studied using a Monte Carlo search technique. Two principal conformational motifs were observed for the bicyclic carbocycle in which both faces of the carbonyl appear susceptible to nucleophilic attack. The title compound was synthesized in eight steps from cis-1,5-cyclooctanediol. Additions of nucleophiles (e.g., CH3Li) to the title compound gave adducts in good yields, but with low levels of diastereoselectivity, in agreement with computational prediction.",
author = "Mash, {Eugene A} and Nimkar, {Kalpana S.} and Baron, {James A.}",
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T1 - Diastereoselective manipulations of bicyclo[m.1.0] alkane derivatives. 3. Nucleophilic additions to the carbonyl carbon of (1R,8R)-Bicyclo[6.1.0]nonan-2,6-dione 2-(2S,3S)-1,4-Di-O-methyl-1,2,3,4-butane ketal

AU - Mash, Eugene A

AU - Nimkar, Kalpana S.

AU - Baron, James A.

PY - 1997/7/7

Y1 - 1997/7/7

N2 - Conformations of the title compound were studied using a Monte Carlo search technique. Two principal conformational motifs were observed for the bicyclic carbocycle in which both faces of the carbonyl appear susceptible to nucleophilic attack. The title compound was synthesized in eight steps from cis-1,5-cyclooctanediol. Additions of nucleophiles (e.g., CH3Li) to the title compound gave adducts in good yields, but with low levels of diastereoselectivity, in agreement with computational prediction.

AB - Conformations of the title compound were studied using a Monte Carlo search technique. Two principal conformational motifs were observed for the bicyclic carbocycle in which both faces of the carbonyl appear susceptible to nucleophilic attack. The title compound was synthesized in eight steps from cis-1,5-cyclooctanediol. Additions of nucleophiles (e.g., CH3Li) to the title compound gave adducts in good yields, but with low levels of diastereoselectivity, in agreement with computational prediction.

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