2,2′-Biphenol/B(OH)3 catalyst system for Nazarov cyclization

Kenji Sugimoto; Miyu Oshiro; Ryuhei Hada; Yuji Matsuya

doi:10.1248/cpb.c19-00399

2,2′-Biphenol/B(OH)₃ catalyst system for Nazarov cyclization

Kenji Sugimoto^*, Miyu Oshiro, Ryuhei Hada, Yuji Matsuya

^*Corresponding author for this work

Synthetic and Medicinal Chemistry

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

4 Scopus citations

Abstract

A novel catalyst system—a combination of the readily available 2,2′-biphenol with the inexpensive, nontoxic, and eco-friendly B(OH)₃—promoted the Nazarov cyclization of activated and inactivated divinyl ketones to afford the corresponding cyclopentenones up to 96% yield under, in a cis-selective manner. Compared with the conventional harsh conditions with hazardous reagents, user-friendly method was established with bench-stable and easy-to-handle reagents.

Original language	English
Pages (from-to)	1019-1022
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	67
Issue number	9
DOIs	https://doi.org/10.1248/cpb.c19-00399
State	Published - 2019

Keywords

2,2′-biphenol
Boric acid
Cyclopentenone
Nazarov cyclization

ASJC Scopus subject areas

General Chemistry
Drug Discovery

Access to Document

10.1248/cpb.c19-00399

Cite this

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title = "2,2′-Biphenol/B(OH)3 catalyst system for Nazarov cyclization",

abstract = "A novel catalyst system—a combination of the readily available 2,2′-biphenol with the inexpensive, nontoxic, and eco-friendly B(OH)3—promoted the Nazarov cyclization of activated and inactivated divinyl ketones to afford the corresponding cyclopentenones up to 96% yield under, in a cis-selective manner. Compared with the conventional harsh conditions with hazardous reagents, user-friendly method was established with bench-stable and easy-to-handle reagents.",

keywords = "2,2′-biphenol, Boric acid, Cyclopentenone, Nazarov cyclization",

author = "Kenji Sugimoto and Miyu Oshiro and Ryuhei Hada and Yuji Matsuya",

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AU - Sugimoto, Kenji

AU - Oshiro, Miyu

AU - Hada, Ryuhei

AU - Matsuya, Yuji

PY - 2019

Y1 - 2019

N2 - A novel catalyst system—a combination of the readily available 2,2′-biphenol with the inexpensive, nontoxic, and eco-friendly B(OH)3—promoted the Nazarov cyclization of activated and inactivated divinyl ketones to afford the corresponding cyclopentenones up to 96% yield under, in a cis-selective manner. Compared with the conventional harsh conditions with hazardous reagents, user-friendly method was established with bench-stable and easy-to-handle reagents.

AB - A novel catalyst system—a combination of the readily available 2,2′-biphenol with the inexpensive, nontoxic, and eco-friendly B(OH)3—promoted the Nazarov cyclization of activated and inactivated divinyl ketones to afford the corresponding cyclopentenones up to 96% yield under, in a cis-selective manner. Compared with the conventional harsh conditions with hazardous reagents, user-friendly method was established with bench-stable and easy-to-handle reagents.

KW - 2,2′-biphenol

KW - Boric acid

KW - Cyclopentenone

KW - Nazarov cyclization

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