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j.tetlet.2014.11.105.pdf | 880.33 kB | Adobe PDF | 見る/開く |
タイトル: | Contiguous radical pivaloyloxymethylation–directed C(sp3)–H iodination of N-tosyl cycloalkanecarbaldimine |
著者: | Fujii, Shintaro Nakano, Mayu Yamaoka, Yousuke Takasu, Kiyosei https://orcid.org/0000-0002-1798-7919 (unconfirmed) Yamada, Ken-ichi Tomioka, Kiyoshi |
著者名の別形: | 山田, 健一 |
キーワード: | Radical reactions Cascade reactions Csingle bondH functionalization Aminyl radical generation Csingle bondC bond formation |
発行日: | Jun-2015 |
出版者: | Elsevier Ltd. |
誌名: | Tetrahedron Letters |
巻: | 56 |
号: | 23 |
開始ページ: | 3086 |
終了ページ: | 3089 |
抄録: | A reaction of N-tosyl cycloalkanecarbaldimines with iodomethyl pivalate was initiated by triethylborane to give pivaloyloxymethylated products bearing 3-iodocycloalkyl groups. Radical addition of pivaloyloxymethyl to imines generates aminyl radicals, which then regioselectively cleave Csingle bondH bonds at the 3-position of the cycloalkane moieties. The resulting carbon-centered radicals are trapped with iodine. DFT calculations rationalized stereo- and regioselectivity. |
記述: | Available online 27 November 2014 |
著作権等: | © 2014. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/ The full-text file will be made open to the public on 27 November 2016 in accordance with publisher's 'Terms and Conditions for Self-Archiving'. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 This is not the published version. Please cite only the published version. |
URI: | http://hdl.handle.net/2433/202095 |
DOI(出版社版): | 10.1016/j.tetlet.2014.11.105 |
出現コレクション: | 学術雑誌掲載論文等 |
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