Highly enantioselective reactions of α-sulfonyl carbanions of trifluoromethyl sulfones

Shuichi Nakamura; Norimune Hirata; Takeshi Kita; Ryusuke Yamada; Daisuke Nakane; Norio Shibata; Takeshi Toru

doi:10.1002/anie.200702185

Highly enantioselective reactions of α-sulfonyl carbanions of trifluoromethyl sulfones

Shuichi Nakamura, Norimune Hirata, Takeshi Kita, Ryusuke Yamada, Daisuke Nakane, Norio Shibata, Takeshi Toru

Department of Chemistry

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

28 Citations (Scopus)

Abstract

(Chemical Equation Presented) Making a resolution: The catalytic enantioselective reaction of lithiated benzyl trifluoromethyl sulfone with aldehydes delivers products with excellent diastereoselectivity as well as high enantioselectivity. Fluorination of the sulfone with N-fluorobenzensulfonimide in the presence of a stoichiometric amount of bis(oxazoline)s resulted in extremely high enantioselectivity (up to 99% ee, see scheme).

Original language	English
Pages (from-to)	7648-7650
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	40
DOIs	https://doi.org/10.1002/anie.200702185
Publication status	Published - 2007

Keywords

Asymmetric synthesis
Carbanions
Enantioselectivity
Homogeneous catalysis
Sulfones

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title = "Highly enantioselective reactions of α-sulfonyl carbanions of trifluoromethyl sulfones",

abstract = "(Chemical Equation Presented) Making a resolution: The catalytic enantioselective reaction of lithiated benzyl trifluoromethyl sulfone with aldehydes delivers products with excellent diastereoselectivity as well as high enantioselectivity. Fluorination of the sulfone with N-fluorobenzensulfonimide in the presence of a stoichiometric amount of bis(oxazoline)s resulted in extremely high enantioselectivity (up to 99\% ee, see scheme).",

keywords = "Asymmetric synthesis, Carbanions, Enantioselectivity, Homogeneous catalysis, Sulfones",

author = "Shuichi Nakamura and Norimune Hirata and Takeshi Kita and Ryusuke Yamada and Daisuke Nakane and Norio Shibata and Takeshi Toru",

year = "2007",

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T1 - Highly enantioselective reactions of α-sulfonyl carbanions of trifluoromethyl sulfones

AU - Nakamura, Shuichi

AU - Hirata, Norimune

AU - Kita, Takeshi

AU - Yamada, Ryusuke

AU - Nakane, Daisuke

AU - Shibata, Norio

AU - Toru, Takeshi

PY - 2007

Y1 - 2007

N2 - (Chemical Equation Presented) Making a resolution: The catalytic enantioselective reaction of lithiated benzyl trifluoromethyl sulfone with aldehydes delivers products with excellent diastereoselectivity as well as high enantioselectivity. Fluorination of the sulfone with N-fluorobenzensulfonimide in the presence of a stoichiometric amount of bis(oxazoline)s resulted in extremely high enantioselectivity (up to 99% ee, see scheme).

AB - (Chemical Equation Presented) Making a resolution: The catalytic enantioselective reaction of lithiated benzyl trifluoromethyl sulfone with aldehydes delivers products with excellent diastereoselectivity as well as high enantioselectivity. Fluorination of the sulfone with N-fluorobenzensulfonimide in the presence of a stoichiometric amount of bis(oxazoline)s resulted in extremely high enantioselectivity (up to 99% ee, see scheme).

KW - Asymmetric synthesis

KW - Carbanions

KW - Enantioselectivity

KW - Homogeneous catalysis

KW - Sulfones

UR - https://www.scopus.com/pages/publications/35048820896

U2 - 10.1002/anie.200702185

DO - 10.1002/anie.200702185

M3 - Article

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AN - SCOPUS:35048820896

SN - 1433-7851

VL - 46

SP - 7648

EP - 7650

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 40

ER -

Highly enantioselective reactions of α-sulfonyl carbanions of trifluoromethyl sulfones

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Keywords

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