Publication: An Efficient Directed Claisen Reaction Allows for Rapid Construction of 5,6-Disubstituted 1,3-Dioxin-4-ones
Date
2015
Published Version
Journal Title
Journal ISSN
Volume Title
Publisher
Thieme Publishing Group
The Harvard community has made this article openly available. Please share how this access benefits you.
Citation
Myers, Andrew, Ziyang Zhang, and Yoshiaki Kitamura. 2015. “An Efficient Directed Claisen Reaction Allows for Rapid Construction of 5,6-Disubstituted 1,3-Dioxin-4-Ones.” Synthesis 47 (18) (August 3): 2709–2712. doi:10.1055/s-0034-1378822.
Research Data
Abstract
An efficient directed Claisen reaction between tert-butyl propionate and phenyl propionate is described. This enables a practical synthesis of 6-ethyl-2,2,5-trimethyl-4H-1,3-dioxin-4-one and thereby (Z)-[(4-ethylidene-2,2,5-trimethyl-4H-1,3-dioxin-6-yl)oxy]trimethylsilane, a key building block in our synthesis of macrolide antibiotics. The three-step route elaborated for the preparation of the latter substance requires no chromatography and is amenable to large-scale synthesis.
Description
Other Available Sources
Keywords
Terms of Use
Metadata Only