title: Practical asymmetric conjugate alkynylation of Meldrum's acid-derived acceptors: access to chiral beta-alkynyl acids.
abstract: The enantioselective conjugate addition of alkynyl nucleophiles has been a long-standing challenge in synthetic chemistry. This paper describes a highly practical asymmetric conjugate alkynylation of Meldrum's acid-derived acceptors using cinchonidine (<$100/kg) as the chiral mediator. The process provides practical access to chiral beta-alkynyl acids. Noteworthy attributes of the method are its broad scope, high functional-group compatibility, and ease of scalability.
authors.affiliation: Department of Chemical Process Research and Development, Amgen Inc., One Amgen Center Drive, Thousand Oaks, California 91320, USA. scui@amgen.com
authors.forename: Sheng
authors.initials: S
authors.lastname: Cui
authors.forename: Shawn D
authors.initials: SD
authors.lastname: Walker
authors.forename: Jacqueline C S
authors.initials: JC
authors.lastname: Woo
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Borths
authors.forename: Herschel
authors.initials: H
authors.lastname: Mukherjee
authors.forename: Maosheng J
authors.initials: MJ
authors.lastname: Chen
authors.forename: Margaret M
authors.initials: MM
authors.lastname: Faul
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D004146:Dioxanes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D002264:Carboxylic Acids; D004146:Dioxanes; C076489:Meldrum's acid