Chiral pyrophosphoric acid catalysts for the para-selective and enantioselective aza-friedel-crafts reaction of phenols

Haruka Okamoto; Kohei Toh; Takuya Mochizuki; Hidefumi Nakatsuji; Akira Sakakura; Manabu Hatano; Kazuaki Ishihara

doi:10.1055/s-0037-1610250

Chiral pyrophosphoric acid catalysts for the para-selective and enantioselective aza-friedel-crafts reaction of phenols

Haruka Okamoto, Kohei Toh, Takuya Mochizuki, Hidefumi Nakatsuji, Akira Sakakura, Manabu Hatano, Kazuaki Ishihara

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

8 Citations (Scopus)

Abstract

Chiral BINOL-derived pyrophosphoric acid catalysts were developed and used for the regio- and enantioselective aza-Friedel-Crafts reaction of phenols with aldimines. ortho/para-Directing phenols could react at the para-position selectively with moderate to good enantioselectivities. Moreover, the gram-scale transformation of a product into the key intermediate for the antifungal agent (R)-bifonazole was demonstrated.

Original language	English
Pages (from-to)	4577-4590
Number of pages	14
Journal	Synthesis (Germany)
Volume	50
Issue number	23
DOIs	https://doi.org/10.1055/s-0037-1610250
Publication status	Published - 2018

Keywords

Aza-Friedel-Crafts reaction
Brønsted acid
Or-ganocatalyst
Phenol
Phosphoric acid
Pyrophosphoric acid
Regio-selectivity

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-0037-1610250

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title = "Chiral pyrophosphoric acid catalysts for the para-selective and enantioselective aza-friedel-crafts reaction of phenols",

abstract = "Chiral BINOL-derived pyrophosphoric acid catalysts were developed and used for the regio- and enantioselective aza-Friedel-Crafts reaction of phenols with aldimines. ortho/para-Directing phenols could react at the para-position selectively with moderate to good enantioselectivities. Moreover, the gram-scale transformation of a product into the key intermediate for the antifungal agent (R)-bifonazole was demonstrated.",

keywords = "Aza-Friedel-Crafts reaction, Br{\o}nsted acid, Or-ganocatalyst, Phenol, Phosphoric acid, Pyrophosphoric acid, Regio-selectivity",

author = "Haruka Okamoto and Kohei Toh and Takuya Mochizuki and Hidefumi Nakatsuji and Akira Sakakura and Manabu Hatano and Kazuaki Ishihara",

note = "Funding Information: This work was financially supported by JSPS KAKENHI Grant Numbers JP26288046, JP17H03054, and JP15H05810 in Precisely Designed Catalysts with Customized Scaffolding.() Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart · New York.",

year = "2018",

doi = "10.1055/s-0037-1610250",

language = "English",

volume = "50",

pages = "4577--4590",

journal = "Synthesis",

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publisher = "Georg Thieme Verlag",

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T1 - Chiral pyrophosphoric acid catalysts for the para-selective and enantioselective aza-friedel-crafts reaction of phenols

AU - Okamoto, Haruka

AU - Toh, Kohei

AU - Mochizuki, Takuya

AU - Nakatsuji, Hidefumi

AU - Sakakura, Akira

AU - Hatano, Manabu

AU - Ishihara, Kazuaki

N1 - Funding Information: This work was financially supported by JSPS KAKENHI Grant Numbers JP26288046, JP17H03054, and JP15H05810 in Precisely Designed Catalysts with Customized Scaffolding.() Publisher Copyright: © Georg Thieme Verlag Stuttgart · New York.

PY - 2018

Y1 - 2018

N2 - Chiral BINOL-derived pyrophosphoric acid catalysts were developed and used for the regio- and enantioselective aza-Friedel-Crafts reaction of phenols with aldimines. ortho/para-Directing phenols could react at the para-position selectively with moderate to good enantioselectivities. Moreover, the gram-scale transformation of a product into the key intermediate for the antifungal agent (R)-bifonazole was demonstrated.

AB - Chiral BINOL-derived pyrophosphoric acid catalysts were developed and used for the regio- and enantioselective aza-Friedel-Crafts reaction of phenols with aldimines. ortho/para-Directing phenols could react at the para-position selectively with moderate to good enantioselectivities. Moreover, the gram-scale transformation of a product into the key intermediate for the antifungal agent (R)-bifonazole was demonstrated.

KW - Aza-Friedel-Crafts reaction

KW - Brønsted acid

KW - Or-ganocatalyst

KW - Phenol

KW - Phosphoric acid

KW - Pyrophosphoric acid

KW - Regio-selectivity

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DO - 10.1055/s-0037-1610250

M3 - Article

AN - SCOPUS:85060096628

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VL - 50

SP - 4577

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JO - Synthesis

JF - Synthesis

IS - 23

ER -

Chiral pyrophosphoric acid catalysts for the para-selective and enantioselective aza-friedel-crafts reaction of phenols

Abstract

Keywords

ASJC Scopus subject areas

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