Enantioselective bromocyclization of 2-geranylphenols induced by chiral phosphite-urea bifunctional catalysts

Yasuhiro Sawamura; Yoshihiro Ogura; Hidefumi Nakatsuji; Akira Sakakura; Kazuaki Ishihara

doi:10.1039/c6cc00229c

Enantioselective bromocyclization of 2-geranylphenols induced by chiral phosphite-urea bifunctional catalysts

Yasuhiro Sawamura, Yoshihiro Ogura, Hidefumi Nakatsuji, Akira Sakakura, Kazuaki Ishihara

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

26 Citations (Scopus)

Abstract

Chiral phosphite-urea bifunctional catalysts have been developed for the enantioselective bromocyclization of 2-geranylphenols with N-bromophthalimide (NBP) for the first time. The chiral triaryl phosphite moiety activates NBP to generate a bromophosphonium ion. On the other hand, the urea moiety interacts with a hydroxyl group of the substrate through hydrogen bonding interactions. Enantioselectivity is effectively induced through two-point attractive interactions between the catalyst and the substrate.

Original language	English
Pages (from-to)	6068-6071
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	36
DOIs	https://doi.org/10.1039/c6cc00229c
Publication status	Published - 2016

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "Enantioselective bromocyclization of 2-geranylphenols induced by chiral phosphite-urea bifunctional catalysts",

abstract = "Chiral phosphite-urea bifunctional catalysts have been developed for the enantioselective bromocyclization of 2-geranylphenols with N-bromophthalimide (NBP) for the first time. The chiral triaryl phosphite moiety activates NBP to generate a bromophosphonium ion. On the other hand, the urea moiety interacts with a hydroxyl group of the substrate through hydrogen bonding interactions. Enantioselectivity is effectively induced through two-point attractive interactions between the catalyst and the substrate.",

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T1 - Enantioselective bromocyclization of 2-geranylphenols induced by chiral phosphite-urea bifunctional catalysts

AU - Sawamura, Yasuhiro

AU - Ogura, Yoshihiro

AU - Nakatsuji, Hidefumi

AU - Sakakura, Akira

AU - Ishihara, Kazuaki

PY - 2016

Y1 - 2016

N2 - Chiral phosphite-urea bifunctional catalysts have been developed for the enantioselective bromocyclization of 2-geranylphenols with N-bromophthalimide (NBP) for the first time. The chiral triaryl phosphite moiety activates NBP to generate a bromophosphonium ion. On the other hand, the urea moiety interacts with a hydroxyl group of the substrate through hydrogen bonding interactions. Enantioselectivity is effectively induced through two-point attractive interactions between the catalyst and the substrate.

AB - Chiral phosphite-urea bifunctional catalysts have been developed for the enantioselective bromocyclization of 2-geranylphenols with N-bromophthalimide (NBP) for the first time. The chiral triaryl phosphite moiety activates NBP to generate a bromophosphonium ion. On the other hand, the urea moiety interacts with a hydroxyl group of the substrate through hydrogen bonding interactions. Enantioselectivity is effectively induced through two-point attractive interactions between the catalyst and the substrate.

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Enantioselective bromocyclization of 2-geranylphenols induced by chiral phosphite-urea bifunctional catalysts

Abstract

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