ID 113022
Author
Ichio, Hiroaki Hokkaido University
Murakami, Hidetoshi Hokkaido University
Chen, Yen-Chou Tokushima University|Hokkaido University
Takahashi, Tamotsu Hokkaido University
Content Type
Journal Article
Description
A palladium-catalyzed reaction of preparing various endocyclic allenes was developed. The substrates for the reaction were readily available ω-(pronucleophile-tethered)-3-bromo-1,3-alkadienes, and a palladium-catalyst facilitated their unimolecular SN2'-cyclization in the presence of potassium tert-butoxide to give the corresponding 9- to 16-membered endocyclic allenes in fair yields of up to 67% together with the dimeric 16- to 32-membered endocyclic bis-allenes and other oligomeric/polymeric intermolecular reaction products. For higher yields of the monomeric endocyclic allenes, the reaction needed to be conducted under high-dilution conditions. Using a chiral palladium-catalyst, axially chiral endocyclic allenes were obtained in up to 70% ee.
Journal Title
The Journal of Organic Chemistry
ISSN
00223263
15206904
NCID
AA00704100
AA12097242
Publisher
ACS Publications
Volume
82
Issue
14
Start Page
7503
End Page
7511
Published Date
2017-06-22
Remark
This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.7b01204.
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DOI (Published Version)
URL ( Publisher's Version )
FullText File
language
eng
TextVersion
Author
departments
Science and Technology