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Intramolecular Conjugate Addition of α,β-Unsaturated Lactones Having an Alkanenitrile Side Chain: Stereocontrolled Construction of Carbocycles with Quaternary Carbon Atoms
| Title: | Intramolecular Conjugate Addition of α,β-Unsaturated Lactones Having an Alkanenitrile Side Chain: Stereocontrolled Construction of Carbocycles with Quaternary Carbon Atoms |
| Authors: | Yoshimura, Fumihiko Browse this author →KAKEN DB | | Torizuka, Makoto Browse this author | | Mori, Genki Browse this author | | Tanino, Keiji Browse this author →KAKEN DB |
| Keywords: | carbocycles | | cyclization | | Michael addition | | nitriles | | stereoselective synthesis |
| Issue Date: | Jan-2012 |
| Publisher: | Georg Thieme Verlag |
| Journal Title: | Synlett |
| Volume: | 2012 |
| Issue: | 2 |
| Start Page: | 251 |
| End Page: | 254 |
| Publisher DOI: | 10.1055/s-0031-1290074 |
| Abstract: | An efficient method for constructing carbocycles with all-carbon quaternary stereocenters has been developed on the basis of a stereoselective cyclization reaction of α,β-unsaturated lactones having an alkanenitrile side chain. Treatment of the substrate with lithium hexamethyldisilazide (LiHMDS) in the presence of triisopropylsilyl chloride (TIPSCl) led to the generation of the corresponding α-cyano carbanion species which readily underwent an intramolecular conjugate addition reaction. It was found that the combined use of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and triethylamine is also effective for the cyclization reaction without using a strong base. Interestingly, different stereochemical outcomes were observed in the two cyclization methods. |
| Rights: | © 2012 Georg Thieme Verlag |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/51017 |
| Appears in Collections: | 理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 吉村 文彦
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