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

18 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

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ASJC Scopus subject areas

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

Cite this

Sawamura, Y., Ogura, Y., Nakatsuji, H., Sakakura, A., & Ishihara, K. (2016). Enantioselective bromocyclization of 2-geranylphenols induced by chiral phosphite-urea bifunctional catalysts. Chemical Communications, 52(36), 6068-6071. https://doi.org/10.1039/c6cc00229c

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AU - Sawamura, Yasuhiro

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AU - Sakakura, Akira

AU - Ishihara, Kazuaki

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Access to Document

10.1039/c6cc00229c