Empirical method for predicting enantioselectivity in catalytic reactions: demonstration with lipase and oxazaborolidine

Tadashi Ema; Norichika Ura; Masataka Yoshii; Toshinobu Korenaga; Takashi Sakai

doi:10.1016/j.tet.2009.09.058

Empirical method for predicting enantioselectivity in catalytic reactions: demonstration with lipase and oxazaborolidine

Tadashi Ema, Norichika Ura, Masataka Yoshii, Toshinobu Korenaga, Takashi Sakai

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

11 Citations (Scopus)

Abstract

We derived a novel equation capable of predicting the degree of enantioselectivity in a catalytic reaction without any knowledge of the reaction mechanism and/or the transition-state structure, and tested the validity of this equation by changing substrates systematically in the lipase or oxazaborolidine-catalyzed reactions. A good correlation was observed between the predicted and observed E values, and the stereochemistry of the products could be predicted correctly in most cases (28 out of 30).

Original language	English
Pages (from-to)	9583-9591
Number of pages	9
Journal	Tetrahedron
Volume	65
Issue number	46
DOIs	https://doi.org/10.1016/j.tet.2009.09.058
Publication status	Published - Nov 14 2009

Keywords

Enantioselectivity
Lipase
Oxazaborolidine
Prediction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2009.09.058

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title = "Empirical method for predicting enantioselectivity in catalytic reactions: demonstration with lipase and oxazaborolidine",

abstract = "We derived a novel equation capable of predicting the degree of enantioselectivity in a catalytic reaction without any knowledge of the reaction mechanism and/or the transition-state structure, and tested the validity of this equation by changing substrates systematically in the lipase or oxazaborolidine-catalyzed reactions. A good correlation was observed between the predicted and observed E values, and the stereochemistry of the products could be predicted correctly in most cases (28 out of 30).",

keywords = "Enantioselectivity, Lipase, Oxazaborolidine, Prediction",

author = "Tadashi Ema and Norichika Ura and Masataka Yoshii and Toshinobu Korenaga and Takashi Sakai",

note = "Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research from Japan Society for the Promotion of Science (JSPS). We are grateful to the SC-NMR Laboratory of Okayama University for the measurement of NMR spectra. ",

year = "2009",

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doi = "10.1016/j.tet.2009.09.058",

language = "English",

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T1 - Empirical method for predicting enantioselectivity in catalytic reactions

T2 - demonstration with lipase and oxazaborolidine

AU - Ema, Tadashi

AU - Ura, Norichika

AU - Yoshii, Masataka

AU - Korenaga, Toshinobu

AU - Sakai, Takashi

N1 - Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research from Japan Society for the Promotion of Science (JSPS). We are grateful to the SC-NMR Laboratory of Okayama University for the measurement of NMR spectra.

PY - 2009/11/14

Y1 - 2009/11/14

N2 - We derived a novel equation capable of predicting the degree of enantioselectivity in a catalytic reaction without any knowledge of the reaction mechanism and/or the transition-state structure, and tested the validity of this equation by changing substrates systematically in the lipase or oxazaborolidine-catalyzed reactions. A good correlation was observed between the predicted and observed E values, and the stereochemistry of the products could be predicted correctly in most cases (28 out of 30).

AB - We derived a novel equation capable of predicting the degree of enantioselectivity in a catalytic reaction without any knowledge of the reaction mechanism and/or the transition-state structure, and tested the validity of this equation by changing substrates systematically in the lipase or oxazaborolidine-catalyzed reactions. A good correlation was observed between the predicted and observed E values, and the stereochemistry of the products could be predicted correctly in most cases (28 out of 30).

KW - Enantioselectivity

KW - Lipase

KW - Oxazaborolidine

KW - Prediction

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U2 - 10.1016/j.tet.2009.09.058

DO - 10.1016/j.tet.2009.09.058

M3 - Article

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SN - 0040-4020

VL - 65

SP - 9583

EP - 9591

JO - Tetrahedron

JF - Tetrahedron

IS - 46

ER -

Empirical method for predicting enantioselectivity in catalytic reactions: demonstration with lipase and oxazaborolidine

Abstract

Keywords

ASJC Scopus subject areas

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