title: Catalyst-free synthesis of skipped dienes from phosphorus ylides, allylic carbonates, and aldehydes via a one-pot SN2' allylation-Wittig strategy.
abstract: 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.
authors.affiliation: Department of Chemistry, School of Science, and ‡College of Pharmacy, Xi'an Jiaotong University , Xi'an 710049, P. R. China.
authors.forename: Silong
authors.initials: S
authors.lastname: Xu
authors.forename: Shaoying
authors.initials: S
authors.lastname: Zhu
authors.forename: Jian
authors.initials: J
authors.lastname: Shang
authors.forename: Junjie
authors.initials: J
authors.lastname: Zhang
authors.forename: Yuhai
authors.initials: Y
authors.lastname: Tang
authors.forename: Jianwei
authors.initials: J
authors.lastname: Dou
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D002254:Carbonates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010758:Phosphorus / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000475:Alkenes; D002254:Carbonates; D010758:Phosphorus