Catalyst-Free Synthesis of Skipped Dienes from Phosphorus Ylides, Allylic Carbonates, and Aldehydes via a One-Pot SN2' Allylation-Wittig Strategy.
- Resource Type
- Article
- Authors
- Silong Xu; Shaoying Zhu; Jian Shang; Junjie Zhang; Yuhai Tang; Jianwei Dou
- Source
- Journal of Organic Chemistry. 4/18/2014, Vol. 79 Issue 8, p3696-3703. 8p.
- Subject
- *DIOLEFINS
*PHOSPHORANE derivatives
*ALLYL compounds
*CARBONATES
*ALDEHYDES
- Language
- ISSN
- 0022-3263
A catalyst-free allylic alkylation of stabilized phosphorus ylides with allylic carbonates via a regioselective SN2' process is presented. Subsequent one-pot Wittig reaction with both aliphatic and aromatic aldehydes as well as ketenes provides structurally diverse skipped dienes (1,4-dienes) in generally high yields and moderate to excellent stereoselectivity with flexible substituent patterns. This one-pot SN2' allylation-Wittig strategy constitutes a convenient and efficient synthetic method for highly functionalized skipped dienes from readily available starting materials. [ABSTRACT FROM AUTHOR]