Synthetic Method for 2,2'-Disubstituted Fluorinated Binaphthyl Derivatives and Application as Chiral Source in Design of Chiral Mono-Phosphoric Acid Catalyst

Norie Momiyama; Hiroshi Okamoto; Masahiro Shimizu; Masahiro Terada

doi:10.1002/chir.22429

Synthetic Method for 2,2'-Disubstituted Fluorinated Binaphthyl Derivatives and Application as Chiral Source in Design of Chiral Mono-Phosphoric Acid Catalyst

Norie Momiyama, Hiroshi Okamoto, Masahiro Shimizu, Masahiro Terada

SCI - Chemistry

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

10 Citations (Scopus)

Abstract

A practical synthetic method for 2,2'-disubstituted fluorinated binaphthyl derivatives was achieved using magnesium bis(2,2,6,6-tetramethylpiperamide) [Mg(TMP)₂], prepared from LiTMP (2 equiv) and MgBr₂ (1 equiv), which allows for access to a variety of fluorinated binaphthyl compounds. The utility of the fluorinated binaphthyl backbone was evaluated in F₁₀BINOL derived chiral mono-phosphoric acid (R)-19 as the chiral Brønsted acid catalyst. The catalyst (R)-19 performs exceptionally well in the catalytic enantioselective imino-ene reaction, demonstrating the potential of a fluorinated binaphthyl framework. Chirality 27:464-475, 2015.

Original language	English
Pages (from-to)	464-475
Number of pages	12
Journal	Chirality
Volume	27
Issue number	8
DOIs	https://doi.org/10.1002/chir.22429
Publication status	Published - 2015 Aug 1

Keywords

axial chirality
chiral Brønsted acid
chiral phosphoric acid
fluorinated binaphthyl
organocatalyst

ASJC Scopus subject areas

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/chir.22429

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title = "Synthetic Method for 2,2'-Disubstituted Fluorinated Binaphthyl Derivatives and Application as Chiral Source in Design of Chiral Mono-Phosphoric Acid Catalyst",

abstract = "A practical synthetic method for 2,2'-disubstituted fluorinated binaphthyl derivatives was achieved using magnesium bis(2,2,6,6-tetramethylpiperamide) [Mg(TMP)2], prepared from LiTMP (2 equiv) and MgBr2 (1 equiv), which allows for access to a variety of fluorinated binaphthyl compounds. The utility of the fluorinated binaphthyl backbone was evaluated in F10BINOL derived chiral mono-phosphoric acid (R)-19 as the chiral Br{\o}nsted acid catalyst. The catalyst (R)-19 performs exceptionally well in the catalytic enantioselective imino-ene reaction, demonstrating the potential of a fluorinated binaphthyl framework. Chirality 27:464-475, 2015.",

keywords = "axial chirality, chiral Br{\o}nsted acid, chiral phosphoric acid, fluorinated binaphthyl, organocatalyst",

author = "Norie Momiyama and Hiroshi Okamoto and Masahiro Shimizu and Masahiro Terada",

note = "Publisher Copyright: {\textcopyright} 2015 Wiley Periodicals, Inc. {\textcopyright} 2015 Wiley Periodicals, Inc.",

year = "2015",

month = aug,

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doi = "10.1002/chir.22429",

language = "English",

volume = "27",

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journal = "Chirality",

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TY - JOUR

T1 - Synthetic Method for 2,2'-Disubstituted Fluorinated Binaphthyl Derivatives and Application as Chiral Source in Design of Chiral Mono-Phosphoric Acid Catalyst

AU - Momiyama, Norie

AU - Okamoto, Hiroshi

AU - Shimizu, Masahiro

AU - Terada, Masahiro

PY - 2015/8/1

Y1 - 2015/8/1

N2 - A practical synthetic method for 2,2'-disubstituted fluorinated binaphthyl derivatives was achieved using magnesium bis(2,2,6,6-tetramethylpiperamide) [Mg(TMP)2], prepared from LiTMP (2 equiv) and MgBr2 (1 equiv), which allows for access to a variety of fluorinated binaphthyl compounds. The utility of the fluorinated binaphthyl backbone was evaluated in F10BINOL derived chiral mono-phosphoric acid (R)-19 as the chiral Brønsted acid catalyst. The catalyst (R)-19 performs exceptionally well in the catalytic enantioselective imino-ene reaction, demonstrating the potential of a fluorinated binaphthyl framework. Chirality 27:464-475, 2015.

AB - A practical synthetic method for 2,2'-disubstituted fluorinated binaphthyl derivatives was achieved using magnesium bis(2,2,6,6-tetramethylpiperamide) [Mg(TMP)2], prepared from LiTMP (2 equiv) and MgBr2 (1 equiv), which allows for access to a variety of fluorinated binaphthyl compounds. The utility of the fluorinated binaphthyl backbone was evaluated in F10BINOL derived chiral mono-phosphoric acid (R)-19 as the chiral Brønsted acid catalyst. The catalyst (R)-19 performs exceptionally well in the catalytic enantioselective imino-ene reaction, demonstrating the potential of a fluorinated binaphthyl framework. Chirality 27:464-475, 2015.

KW - axial chirality

KW - chiral Brønsted acid

KW - chiral phosphoric acid

KW - fluorinated binaphthyl

KW - organocatalyst

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U2 - 10.1002/chir.22429

DO - 10.1002/chir.22429

M3 - Article

AN - SCOPUS:84937817629

SN - 0899-0042

VL - 27

SP - 464

EP - 475

JO - Chirality

JF - Chirality

IS - 8

ER -

Synthetic Method for 2,2'-Disubstituted Fluorinated Binaphthyl Derivatives and Application as Chiral Source in Design of Chiral Mono-Phosphoric Acid Catalyst

Abstract

Keywords

ASJC Scopus subject areas

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