Enantioselective 5-<i>exo</i>-Fluorocyclization of Ene-Oximes

The enantioselective 5-<i>exo</i>-fluorocyclization of ene-oxime compounds was demonstrated under phase-transfer catalysis. Although deprotonative fluorinations competed, the chemical yields and the ee values of the desired isoxazoline products were generally moderate to good. The absolu...

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Bibliographic Details
Main Authors: Taiki Rouno, Tomoki Niwa, Kousuke Nishibashi, Nobuharu Yamamoto, Hiromichi Egami, Yoshitaka Hamashima
Format: Article
Language:English
Published: MDPI AG 2019-09-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/24/19/3464
Description
Summary:The enantioselective 5-<i>exo</i>-fluorocyclization of ene-oxime compounds was demonstrated under phase-transfer catalysis. Although deprotonative fluorinations competed, the chemical yields and the ee values of the desired isoxazoline products were generally moderate to good. The absolute stereochemistry of the major isomer was determined to be <i>S</i> by comparison with the literature after transformation of the product to the corresponding iodinated isoxazoline.
ISSN:1420-3049