title: General, robust, and stereocomplementary preparation of alpha,beta-disubstituted alpha,beta-unsaturated esters.
abstract: An (E)- and (Z)-stereocomplementary preparative method for alpha,beta-disubstituted alpha,beta-unsaturated esters is performed via three general and robust reaction sequences: (i) Ti-Claisen condensation (formylation) of esters to give alpha-formyl esters (12 examples, 60-99%), (ii) (E)- and (Z)-stereocomplementary enol p-toluenesulfonylation (tosylation) using TsCl-N-methylimidazole (NMI)-Et(3)N and LiOH (24 examples, 82-99%), and (iii) stereoretentive Suzuki-Miyaura cross-coupling (18 examples, 64-96%).
authors.affiliation: Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan.
authors.forename: Hidefumi
authors.initials: H
authors.lastname: Nakatsuji
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Nishikado
authors.forename: Kanako
authors.initials: K
authors.lastname: Ueno
authors.forename: Yoo
authors.initials: Y
authors.lastname: Tanabe
mesh_terms: D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D004952:Esters