Asymmetric catalysis of ene-type reaction with fluoral by chiral titanium complex: A semi-empirical and ab-initio analysis of ene reactivity

Koichi Mikami; Tomoko Yajima; Masahiro Terada; Tadafumi Uchimaru

doi:10.1016/S0040-4039(00)60408-2

Asymmetric catalysis of ene-type reaction with fluoral by chiral titanium complex: A semi-empirical and ab-initio analysis of ene reactivity

Koichi Mikami, Tomoko Yajima, Masahiro Terada, Tadafumi Uchimaru

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

50 Citations (Scopus)

Abstract

The chiral titanium complex-catalyzed ene-type reaction with fluoral is shown to serve as an efficient route for the asymmetric synthesis of CF₃-substituted compounds of biological and synthetic importance in extremely high enantiomeric excesses (>95% ee). The ene reactivity of trihaloacetaldehyde including fluoral is estimated in terms of the balance of LUMO energy level vs. electron density on the carbonyl carbon.

Original language	English
Pages (from-to)	7591-7594
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	47
DOIs	https://doi.org/10.1016/S0040-4039(00)60408-2
Publication status	Published - 1993 Nov 19
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "The chiral titanium complex-catalyzed ene-type reaction with fluoral is shown to serve as an efficient route for the asymmetric synthesis of CF3-substituted compounds of biological and synthetic importance in extremely high enantiomeric excesses (>95% ee). The ene reactivity of trihaloacetaldehyde including fluoral is estimated in terms of the balance of LUMO energy level vs. electron density on the carbonyl carbon.",

author = "Koichi Mikami and Tomoko Yajima and Masahiro Terada and Tadafumi Uchimaru",

year = "1993",

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doi = "10.1016/S0040-4039(00)60408-2",

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T1 - Asymmetric catalysis of ene-type reaction with fluoral by chiral titanium complex

T2 - A semi-empirical and ab-initio analysis of ene reactivity

AU - Mikami, Koichi

AU - Yajima, Tomoko

AU - Terada, Masahiro

AU - Uchimaru, Tadafumi

PY - 1993/11/19

Y1 - 1993/11/19

N2 - The chiral titanium complex-catalyzed ene-type reaction with fluoral is shown to serve as an efficient route for the asymmetric synthesis of CF3-substituted compounds of biological and synthetic importance in extremely high enantiomeric excesses (>95% ee). The ene reactivity of trihaloacetaldehyde including fluoral is estimated in terms of the balance of LUMO energy level vs. electron density on the carbonyl carbon.

AB - The chiral titanium complex-catalyzed ene-type reaction with fluoral is shown to serve as an efficient route for the asymmetric synthesis of CF3-substituted compounds of biological and synthetic importance in extremely high enantiomeric excesses (>95% ee). The ene reactivity of trihaloacetaldehyde including fluoral is estimated in terms of the balance of LUMO energy level vs. electron density on the carbonyl carbon.

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U2 - 10.1016/S0040-4039(00)60408-2

DO - 10.1016/S0040-4039(00)60408-2

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EP - 7594

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 47

ER -

Asymmetric catalysis of ene-type reaction with fluoral by chiral titanium complex: A semi-empirical and ab-initio analysis of ene reactivity

Abstract

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