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Asymmetric cyclization of 2-alkenylphenols. A comparative study on the use of palladium(II) and titanium(IV) complexes |
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| Authors: | Takahiro Hosokawa Takanori Kono Toru Shinohara Shun-Ichi Murahashi |
| Affiliation: | Department of Chemistry, Faculty of Engineering Science, Osaka University, Machikaneyama, Toyonaka, Osaka 560 Japan |
| Abstract: | The oxidative cyclization of 2-(3-pentenyl)phenol catalyzed by [(η3-pinene)PdOAc]2 gives optically active (+)-2-vinylchroman (25% e.e.), while (−)-2-(1-hydroxyethyl)chroman (56% e.e.) is formed as a single diastereomer upon treatment with t-BuOOH in the presence of Ti(OiPr)4 and -(+)-diethyl tartrate. 2-(2-Butenyl)phenol also undergoes the Ti-promoted asymmetric cyclization to give (2S,1′R)-(−)-2-(1-hydroxyethyl)-2,3-dihydrobenzofuran (29% e.e.). |
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