Remarkable solvent effect on the enantioface selectivity in the Diels- Alder reaction catalyzed by an aluminum complex of a newly prepared chiral menthol derivative

Go Naraku; Kiyoto Hori; Yoshio Ito; Tsutomu Katsuki

doi:10.1016/S0040-4039(97)10202-7

Remarkable solvent effect on the enantioface selectivity in the Diels- Alder reaction catalyzed by an aluminum complex of a newly prepared chiral menthol derivative

Go Naraku, Kiyoto Hori, Yoshio Ito, Tsutomu Katsuki

Organic and Biological Chemistry

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

Reversal of enantioface selectivity was observed by merely switching the solvent from CH₂Cl₂ (enantiomer ratio of the adduct = 91:9) to THF (14:86) in the asymmetric Diels-Alder reaction catalyzed by the aluminum complex of a newly prepared chiral menthol derivative. Negative nonlinear effect on the relationship between enantiomeric excesses of the reaction product and optical purities of the ligand was observed for the reaction in CH₂Cl₂ whilst linear relationship for that in THF.

Original language	English
Pages (from-to)	8231-8232
Number of pages	2
Journal	Tetrahedron Letters
Volume	38
Issue number	47
DOIs	https://doi.org/10.1016/S0040-4039(97)10202-7
Publication status	Published - Nov 24 1997

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Remarkable solvent effect on the enantioface selectivity in the Diels- Alder reaction catalyzed by an aluminum complex of a newly prepared chiral menthol derivative",

abstract = "Reversal of enantioface selectivity was observed by merely switching the solvent from CH2Cl2 (enantiomer ratio of the adduct = 91:9) to THF (14:86) in the asymmetric Diels-Alder reaction catalyzed by the aluminum complex of a newly prepared chiral menthol derivative. Negative nonlinear effect on the relationship between enantiomeric excesses of the reaction product and optical purities of the ligand was observed for the reaction in CH2Cl2 whilst linear relationship for that in THF.",

author = "Go Naraku and Kiyoto Hori and Yoshio Ito and Tsutomu Katsuki",

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T1 - Remarkable solvent effect on the enantioface selectivity in the Diels- Alder reaction catalyzed by an aluminum complex of a newly prepared chiral menthol derivative

AU - Naraku, Go

AU - Hori, Kiyoto

AU - Ito, Yoshio

AU - Katsuki, Tsutomu

PY - 1997/11/24

Y1 - 1997/11/24

N2 - Reversal of enantioface selectivity was observed by merely switching the solvent from CH2Cl2 (enantiomer ratio of the adduct = 91:9) to THF (14:86) in the asymmetric Diels-Alder reaction catalyzed by the aluminum complex of a newly prepared chiral menthol derivative. Negative nonlinear effect on the relationship between enantiomeric excesses of the reaction product and optical purities of the ligand was observed for the reaction in CH2Cl2 whilst linear relationship for that in THF.

AB - Reversal of enantioface selectivity was observed by merely switching the solvent from CH2Cl2 (enantiomer ratio of the adduct = 91:9) to THF (14:86) in the asymmetric Diels-Alder reaction catalyzed by the aluminum complex of a newly prepared chiral menthol derivative. Negative nonlinear effect on the relationship between enantiomeric excesses of the reaction product and optical purities of the ligand was observed for the reaction in CH2Cl2 whilst linear relationship for that in THF.

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U2 - 10.1016/S0040-4039(97)10202-7

DO - 10.1016/S0040-4039(97)10202-7

M3 - Article

AN - SCOPUS:0030691198

VL - 38

SP - 8231

EP - 8232

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 47

ER -

Remarkable solvent effect on the enantioface selectivity in the Diels- Alder reaction catalyzed by an aluminum complex of a newly prepared chiral menthol derivative

Abstract

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