title: One-pot (1-ethoxycarbonylcyclopropyl)triphenylphosphonium tetrafluoroborate ring-opening and Wittig reaction.
abstract: An efficient method was developed for the synthesis of 2-methylene-4-substituted ethyl butyrates via cyclopropyl opening followed by a Wittig reaction. The desired products were formed in a two-step, one-pot reaction sequence. Alternatively, the key intermediate ylide 2 was isolable and could be stored under oxygen-free conditions and subsequently utilized. A variety of nucleophiles were found to open the commercially available cyclopropane 1. The resulting ylide reacted with aldehydes to provide E-olefinic products.
authors.affiliation: Antibacterial Chemistry, Worldwide Research & Development, Pfizer, Inc., Eastern Point Road, Groton, Connecticut 06340, USA. seungwon.chung@pfizer.com
authors.forename: Seung Won
authors.initials: SW
authors.lastname: Chung
authors.forename: Mark S
authors.initials: MS
authors.lastname: Plummer
authors.forename: Laura A
authors.initials: LA
authors.lastname: McAllister
authors.forename: Robert M
authors.initials: RM
authors.lastname: Oliver
authors.forename: Joseph A
authors.initials: JA
authors.lastname: Abramite
authors.forename: Yue
authors.initials: Y
authors.lastname: Shen
authors.forename: Jianmin
authors.initials: J
authors.lastname: Sun
authors.forename: Daniel P
authors.initials: DP
authors.lastname: Uccello
authors.forename: Joel T
authors.initials: JT
authors.lastname: Arcari
authors.forename: Loren M
authors.initials: LM
authors.lastname: Price
authors.forename: Justin I
authors.initials: JI
authors.lastname: Montgomery
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001881:Borates / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*
chemical_list: C569252:(1-ethoxycarbonylcyclopropyl)triphenylphosphonium tetrafluoroborate; D000447:Aldehydes; D001881:Borates; D009943:Organophosphorus Compounds