title: Construction of successive chiral centers adjacent to a chiral tetraalkylated quaternary center using an asymmetric aldol reaction.
abstract: The aldol reaction of 2″ with a variety of different aldehydes gave the corresponding β-lactones 4 bearing successive asymmetric centers adjacent to a chiral tetraalkylated quaternary center or the (E)-alkenes 8. The use of electronically neutral or electron-deficient aldehydes led to 4 in excellent yields with high diastereoselectivities, whereas electron-rich aldehydes performed poorly and underwent decarboxylation to afford 8.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan. esumi@ph.bunri-u.ac.jp
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Esumi
authors.forename: Chihiro
authors.initials: C
authors.lastname: Yamamoto
authors.forename: Yuri
authors.initials: Y
authors.lastname: Tsugawa
authors.forename: Masao
authors.initials: M
authors.lastname: Toyota
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Asakawa
authors.forename: Yoshiyasu
authors.initials: Y
authors.lastname: Fukuyama
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D007783:Lactones