Solvent-dependent stereochemical anomaly in the nucleophilic addition of ester-derived enolate to bicyclo[3,3,0]octan-2-one system of diacetone glucos-3-ulose

Noriaki Yamauchi, Masashi Kishida, Keiju Sawada, Yuji Ohashi, Tadashi Eguchi, Katsumi Kakinuma

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Solvent-dependent anomalous stereoselectivity was observed in the nucleophilic addition of ester enolate to the bicyclo[3,3,0]octane-2-one system of 1,2:5,6-di-O-isopropyli-dene-α-D-glucofuranulose. While most of the addition took place to the β-face of the carbonyl, the senecioate-derived enolate surprisingly preferred α-face attack in ether solvent in contrast to β-face attack in THF.

Original languageEnglish
Pages (from-to)475-476
Number of pages2
JournalChemistry Letters
Issue number6
DOIs
Publication statusPublished - Jan 1 1998
Externally publishedYes

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Esters
Stereoselectivity
Ether
octane

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Solvent-dependent stereochemical anomaly in the nucleophilic addition of ester-derived enolate to bicyclo[3,3,0]octan-2-one system of diacetone glucos-3-ulose. / Yamauchi, Noriaki; Kishida, Masashi; Sawada, Keiju; Ohashi, Yuji; Eguchi, Tadashi; Kakinuma, Katsumi.

In: Chemistry Letters, No. 6, 01.01.1998, p. 475-476.

Research output: Contribution to journalArticle

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