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Title: Contiguous radical pivaloyloxymethylation–directed C(sp3)–H iodination of N-tosyl cycloalkanecarbaldimine
Authors: Fujii, Shintaro
Nakano, Mayu
Yamaoka, Yousuke
Takasu, Kiyosei  kyouindb  KAKEN_id  orcid (unconfirmed)
Yamada, Ken-ichi
Tomioka, Kiyoshi
Author's alias: 山田, 健一
Keywords: Radical reactions
Cascade reactions
Csingle bondH functionalization
Aminyl radical generation
Csingle bondC bond formation
Issue Date: Jun-2015
Publisher: Elsevier Ltd.
Journal title: Tetrahedron Letters
Volume: 56
Issue: 23
Start page: 3086
End page: 3089
Abstract: 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.
Description: Available online 27 November 2014
Rights: © 2014. This manuscript version is made available under the CC-BY-NC-ND 4.0 license
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'.
This is not the published version. Please cite only the published version.
DOI(Published Version): 10.1016/j.tetlet.2014.11.105
Appears in Collections:Journal Articles

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