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タイトル: | Catalytic discrimination between formyl groups in regio-and stereoselective intramolecular cross-Aldol reactions |
著者: | Baba, Tomonori Yamamoto, Junya Hayashi, Kazuhiro Sato, Makoto Yamanaka, Masahiro Kawabata, Takeo https://orcid.org/0000-0002-9959-0420 (unconfirmed) Furuta, Takumi |
著者名の別形: | 川端, 猛夫 古田, 巧 |
発行日: | 22-Feb-2016 |
出版者: | Royal Society of Chemistry (RSC) |
誌名: | Chemical Science |
巻: | 7 |
開始ページ: | 3791 |
終了ページ: | 3797 |
抄録: | Catalytic discrimination between inequivalent formyl groups was achieved using an aniline-Type acid-base catalyst for the regio-, diastereo-, and enantioselective intramolecular cross-Aldol reactions of enolizable dials. Although l-proline gave a mixture of the regio-and stereoisomeric products in the presence of an N-containing 1, 6-dial, the aniline-Type catalyst afforded anti-3, 4-disubstituted pyrrolidine in high regio-, and stereoselectivity beyond the background reaction, which led to the regioisomeric 2, 3-disubstituted products. The mild reactivity of the aniline-Type amine facilitated catalytic discrimination between the inequivalent formyl groups. Kinetic isotope effect studies and reductive amination experiments suggested that the regioselectivity was controlled under the enamine-forming steps. |
著作権等: | © The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. |
URI: | http://hdl.handle.net/2433/216556 |
DOI(出版社版): | 10.1039/c5sc04594k |
PubMed ID: | 30155021 |
出現コレクション: | 学術雑誌掲載論文等 |
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