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

doi:10.1246/cl.1998.475

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 journal › Article › peer-review

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 language	English
Pages (from-to)	475-476
Number of pages	2
Journal	Chemistry Letters
Issue number	6
DOIs	https://doi.org/10.1246/cl.1998.475
Publication status	Published - 1998
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1246/cl.1998.475

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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.",

author = "Noriaki Yamauchi and Masashi Kishida and Keiju Sawada and Yuji Ohashi and Tadashi Eguchi and Katsumi Kakinuma",

year = "1998",

doi = "10.1246/cl.1998.475",

language = "English",

pages = "475--476",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "The Chemical Society of Japan",

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T1 - 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

AU - Yamauchi, Noriaki

AU - Kishida, Masashi

AU - Sawada, Keiju

AU - Ohashi, Yuji

AU - Eguchi, Tadashi

AU - Kakinuma, Katsumi

PY - 1998

Y1 - 1998

N2 - 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.

AB - 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.

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JO - Chemistry Letters

JF - Chemistry Letters

IS - 6

ER -

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

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