Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5271212 | Tetrahedron Letters | 2013 | 4 Pages |
Abstract
ZnI2 was found to promote regio- and stereoselective substitution of γ,γ-disubstituted secondary allylic picolinates with alkylcopper reagents derived from alkyl-MgBr and CuBr·Me2S in a 2:1 ratio to furnish quaternary carbon centers in good yields. Alkyl groups delivered efficiently were the primary, secondary, and benzyl classes such as Me, Et, Bu, C16H33, Ph(CH2)2, Ph(CH2)3, c-C6H11, and Bn. As an application, allylic picolinates with the (E)- or (Z)-olefin afforded quaternary carbon centers that are the enantiomers of each other.
Graphical abstractDownload full-size image
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Chao Feng, Yuki Kaneko, Yuichi Kobayashi,