title: Pd-catalyzed regioselective and stereospecific Suzuki-Miyaura coupling of allylic carbonates with arylboronic acids.
abstract: The Pd-catalyzed Suzuki-Miyaura coupling reaction of unsymmetric 1,3-disubstituted secondary allylic carbonates with arylboronic acids has been developed in a wet solvent under a base-free system to afford allyl-aryl coupling products in a high level of isolated yields with complete regio- and E/Z-selectivities with good to excellent chemoselectivities. The coupling reaction of optically active allyl carbonates gave allyl-aryl coupling products with excellent enantioselectivities with inversion of the stereochemistry. This coupling method was successfully applied to the synthesis of (S)-naproxen.
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, PR China.
authors.forename: Chenguang
authors.initials: C
authors.lastname: Li
authors.forename: Juxiang
authors.initials: J
authors.lastname: Xing
authors.forename: Jingming
authors.initials: J
authors.lastname: Zhao
authors.forename: Patrick
authors.initials: P
authors.lastname: Huynh
authors.forename: Wanbin
authors.initials: W
authors.lastname: Zhang
authors.forename: Pingkai
authors.initials: P
authors.lastname: Jiang
authors.forename: Yong Jian
authors.initials: YJ
authors.lastname: Zhang