title: Monoselective o-C-H Functionalizations of Mandelic Acid and α-Phenylglycine.
abstract: Pd-catalyzed C-H functionalization of mandelic acid and α-phenylglycine is reported. We have developed different protocols for the arylation, iodination, acetoxylation, and olefination of these substrates based on two different (Pd(II)/Pd(IV) and Pd(II)/Pd(0)) catalytic cycles. Four crucial features of these protocols are advantageous for practical applications. First, the α-hydroxyl and amino groups are protected with simple protecting groups such as acetates (Ac, Piv) and carbamates (Boc, Fmoc), respectively. Second, these protocols do not involve installation and removal of a directing group. Third, monoselectivity is accomplished. Fourth, no epimerization occurs at the vulnerable α-chiral centers.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Navid
authors.initials: N
authors.lastname: Dastbaravardeh
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Toba
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Marcus E
authors.initials: ME
authors.lastname: Farmer
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Jin-Quan
authors.initials: JQ
authors.lastname: Yu
mesh_terms: D000475:Alkenes / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D054879:Halogenation; D006859:Hydrogen / Q000737:chemistry*; D008333:Mandelic Acids / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D013379:Substrate Specificity
chemical_list: D000475:Alkenes; D008333:Mandelic Acids; D010165:Palladium; C008852:2-phenylglycine; D002244:Carbon; D006859:Hydrogen; C037938:mandelic acid; D005998:Glycine