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Short Paper | Regular issue | Vol 96, No. 9, 2018, pp.1593-1600
Published online, 8th August, 2018
DOI: 10.3987/COM-18-13932
One-Pot Preparation of Ethyl 2(Z)-4-(Anilinoxy)pentenoate by α-Aminoxylation of Propanal Followed by Z-Selective HWE Reaction and the Study on Its Cyclization Reaction

Kaori Ando,* Mami Takao, Ikumi Oyama, and Kouki Furuta

*Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan

Abstract

A one-pot sequence of α-aminoxylation of n-propanal catalyzed by L-proline followed by the Z-selective Horner-Wadsworth-Emmons reaction was developed. The highly functionalized chiral γ-anilinoxy-Z-α,β-unsaturated ester 6 was obtained in 57-58% yield with 98:2 Z-selectivity from n-propanal in one-pot procedure. The transformation of the anilinoxy group of 6 into a hydroxyl group can be carried out by treatment with catalytic amount of CuSO4 in methanol to give either the corresponding alcohol 8 or chiral γ-valerolactone 4a in moderate yield. Chiral 6-methyl-2-phenyl-2H-1,2-oxazin-3(6H)-one 7 was obtained in 75% yield from 6 by treatment with CSA.