title: Organocatalyzed Enantioselective Direct Mannich Reaction of α-Styrylacetates.
abstract: An organocatalyzed direct Mannich reaction of unactivated α-styrylacetates was realized for the first time. By using a quinidine-derived C6'-urea catalyst, the direct Mannich reaction of α-styrylacetates and N-tosylimines gave the desired β-amino esters in high yields, diastereoselectivities, and ee values. The reaction provides a highly stereoselective (up to 96:4 dr and 97% ee) and the most straightforward synthesis of functionalized N-tosylated β-amino esters. The products can be used as precursors for the highly selective synthesis of tetrahydrofuran derivatives.
authors.affiliation: Department of Chemistry, University of Texas at San Antonio , One UTSA Circle, San Antonio, Texas 78249-0698, United States.
authors.forename: Jie
authors.initials: J
authors.lastname: Guang
authors.affiliation: Department of Chemistry, University of Texas at San Antonio , One UTSA Circle, San Antonio, Texas 78249-0698, United States.
authors.forename: Saroj
authors.initials: S
authors.lastname: Rout
authors.affiliation: Department of Chemistry, University of Texas at San Antonio , One UTSA Circle, San Antonio, Texas 78249-0698, United States.
authors.forename: Manisha
authors.initials: M
authors.lastname: Bihani
authors.affiliation: Department of Chemistry, University of Texas at San Antonio , One UTSA Circle, San Antonio, Texas 78249-0698, United States.
authors.forename: Ariel J
authors.initials: AJ
authors.lastname: Larson
authors.affiliation: Department of Chemistry, University of Texas at San Antonio , One UTSA Circle, San Antonio, Texas 78249-0698, United States.
authors.forename: Hadi D
authors.initials: HD
authors.lastname: Arman
authors.affiliation: Department of Chemistry, University of Texas at San Antonio , One UTSA Circle, San Antonio, Texas 78249-0698, United States.
authors.forename: John C-G
authors.initials: JC
authors.lastname: Zhao
mesh_terms: D000085:Acetates / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D002930:Cinchona Alkaloids; D004952:Esters; D005663:Furans; C018674:tetrahydrofuran