One-Pot Preparation of (E)-α,β-Unsaturated Aldehydes by a Julia-Kocienski Reaction of 2,2-Dimethoxyethyl PT Sulfone Followed by Acid Hydrolysis

Kaori Ando; Haruka Watanabe; Xiaoxian Zhu

doi:10.1021/acs.joc.1c00479

One-Pot Preparation of (E)-α,β-Unsaturated Aldehydes by a Julia-Kocienski Reaction of 2,2-Dimethoxyethyl PT Sulfone Followed by Acid Hydrolysis

J Org Chem. 2021 May 7;86(9):6969-6973. doi: 10.1021/acs.joc.1c00479. Epub 2021 Apr 19.

Authors

Kaori Ando¹, Haruka Watanabe¹, Xiaoxian Zhu¹

Affiliation

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

PMID: 33870683
DOI: 10.1021/acs.joc.1c00479

Abstract

(E)-α,β-Unsaturated aldehydes were synthesized by the Julia-Kocienski reaction of 2,2-dimethoxyethyl 1-phenyl-1H-tetrazol-5-yl (PT) sulfone 3 with various aldehydes, followed by acid hydrolysis. The reaction could be carried out in one pot, and various (E)-α,β-unsaturated aldehydes were obtained in a short time and with high yields.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes*
Hydrolysis
Stereoisomerism
Sulfones*

Substances

Aldehydes
Sulfones