title: Hydrogen-bond-activated palladium-catalyzed allylic alkylation via allylic alkyl ethers: challenging leaving groups.
abstract: C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee).
authors.affiliation: School of Pharmacy and ‡School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University , 800 Dongchuan Road, Shanghai 200240, P. R. China.
authors.forename: Xiaohong
authors.initials: X
authors.lastname: Huo
authors.forename: Mao
authors.initials: M
authors.lastname: Quan
authors.forename: Guoqiang
authors.initials: G
authors.lastname: Yang
authors.forename: Xiaohu
authors.initials: X
authors.lastname: Zhao
authors.forename: Delong
authors.initials: D
authors.lastname: Liu
authors.forename: Yangang
authors.initials: Y
authors.lastname: Liu
authors.forename: Wanbin
authors.initials: W
authors.lastname: Zhang
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000478:Alkylation; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004987:Ethers / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000498:Allyl Compounds; D004987:Ethers; D010165:Palladium