title: Stereoselective Synthesis of Highly Functionalized 2,3-Dihydro-4-pyranones Using Phosphine Oxide as Catalyst.
abstract: 2,3-Dihydro-4-pyranones were synthesized stereoselectively using a chiral phosphine oxide as the catalyst. The phosphine oxide sequentially activated silicon tetrachloride and promoted the double aldol reaction of 4-methoxy-3-buten-2-one with aldehydes. Subsequent stereoselective cyclization afforded the corresponding highly functionalized 2,3-dihydro-4-pyranones bearing three contiguous chiral centers in good yields and with high diastereo- and enantioselectivities.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University.
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Kotani
authors.forename: Shiki
authors.initials: S
authors.lastname: Miyazaki
authors.forename: Kazuya
authors.initials: K
authors.lastname: Kawahara
authors.forename: Yasushi
authors.initials: Y
authors.lastname: Shimoda
authors.forename: Masaharu
authors.initials: M
authors.lastname: Sugiura
authors.forename: Makoto
authors.initials: M
authors.lastname: Nakajima
mesh_terms: D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D010087:Oxides; D010720:Phosphines; D011753:Pyrones; C044646:phosphine