title: Palladium-Catalyzed Asymmetric Allylic Alkylations with Toluene Derivatives as Pronucleophiles.
abstract: The first two highly enantioselective palladium-catalyzed allylic alkylations with benzylic nucleophiles, activated with Cr(CO)3 , have been developed. These methods enable the enantioselective synthesis of α-2-propenyl benzyl motifs, which are important scaffolds in natural products and pharmaceuticals. A variety of cyclic and acyclic allylic carbonates are competent electrophilic partners furnishing the products in excellent enantioselectivity (up to 99 % ee and 92 % yield). This approach was employed to prepare a nonsteroidal anti-inflammatory drug analogue.
authors.affiliation: Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193, P. R. China.|Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, 19104-6323, USA.
authors.forename: Jianyou
authors.initials: J
authors.lastname: Mao
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, 19104-6323, USA.
authors.forename: Jiadi
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193, P. R. China.|Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, 19104-6323, USA.
authors.forename: Hui
authors.initials: H
authors.lastname: Jiang
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, 19104-6323, USA.
authors.forename: Ana
authors.initials: A
authors.lastname: Bellomo
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, 19104-6323, USA.
authors.forename: Mengnan
authors.initials: M
authors.lastname: Zhang
authors.affiliation: Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing, 100193, P. R. China.
authors.forename: Zidong
authors.initials: Z
authors.lastname: Gao
authors.affiliation: Department of Process Chemistry, Merck Research Laboratories, P.O. Box 2000, Rahway, NJ, 07065, USA.
authors.forename: Spencer D
authors.initials: SD
authors.lastname: Dreher
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA, 19104-6323, USA. pwalsh@sas.upenn.edu.
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Walsh
mesh_terms: D000478:Alkylation; D002384:Catalysis; D010165:Palladium / Q000737:chemistry*; D014050:Toluene / Q000737:chemistry*
chemical_list: D014050:Toluene; D010165:Palladium
keywords: allylic compounds; arenes; chromium; enantioselectivity; palladium