title: A switch of facial selectivities using alpha-heteroatom-substituted aldehydes in the vinylogous Mukaiyama aldol reaction.
abstract: The vinylogous Mukaiyama aldol reaction (VMAR) of chiral nonracemic ketene silyl N,O-acetal with various aldehydes is demonstrated. VMAR with alpha-heteroatom-unsubstituted aldehydes proceeded with a high degree of anti-selectivity. In sharp contrast, moderate to high syn-selectivity was observed when alpha-heteroatom-substituted aldehydes were used.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan.
authors.forename: Mariko
authors.initials: M
authors.lastname: Shinoyama
authors.forename: Shin-ichi
authors.initials: S
authors.lastname: Shirokawa
authors.forename: Atsuo
authors.initials: A
authors.lastname: Nakazaki
authors.forename: Susumu
authors.initials: S
authors.lastname: Kobayashi
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000475:Alkenes; D010080:Oxazoles; D012821:Silanes; C116609:3-hydroxybutanal