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Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates
| Title: | Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates |
| Authors: | Yoshida, Masanori Browse this author →KAKEN DB | | Masaki, Erika Browse this author | | Ikehara, Hiroto Browse this author | | Hara, Shoji Browse this author →KAKEN DB |
| Issue Date: | 21-Jul-2012 |
| Publisher: | Royal Society of Chemistry |
| Journal Title: | Organic & Biomolecular Chemistry |
| Volume: | 10 |
| Issue: | 27 |
| Start Page: | 5289 |
| End Page: | 5297 |
| Publisher DOI: | 10.1039/c2ob25413a |
| PMID: | 22678163 |
| Abstract: | Michael addition reaction of α-branched aldehydes to β-nitroacrylates was successfully carried out by using a mixed catalyst consisting of a primary amino acid, L-phenylalanine, and its lithium salt to give β-formyl-β'-nitroesters having a quaternary carbon centre in good yields (up to 85%) with high enantioselectivity (up to 98% ee). By using benzyl β-nitroacrylates as Michael acceptors, the obtained β-formyl-β'-nitroesters were converted into various 4,4-disubstituted pyrrolidine-3-carboxylic acids including analogues of gabapentin (Neurotin®) in one step from the Michael adducts in high yields. |
| Rights: | Org. Biomol. Chem., 2012,10, 5289-5297 - Reproduced by permission of The Royal Society of Chemistry (RSC) |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/52715 |
| Appears in Collections: | 工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 吉田 雅紀
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