title: Asymmetric synthesis of beta-amino carbonyl compounds with N-sulfinyl beta-amino Weinreb amides.
abstract: [reaction: see text] Diverse organometallic reagents readily add to enantiopure N-sulfinyl beta-amino Weinreb amides providing the corresponding, stable, N-sulfinyl beta-amino carbonyl compounds in good to excellent yields. This new methodology represents a general solution to the problem of beta-amino carbonyl syntheses, which are important chiral building blocks and constituents of natural products. N-Sulfinyl beta-amino Weinreb amides are prepared by reaction of the potassium enolate of N-methoxy N-methylacetamide with sulfinimines (N-sulfinyl imines) or lithium N,O-dimethylhydroxylamine with N-sulfinyl beta-amino esters.
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
authors.forename: Franklin A
authors.initials: FA
authors.lastname: Davis
authors.forename: M Brad
authors.initials: MB
authors.lastname: Nolt
authors.forename: Yongzhong
authors.initials: Y
authors.lastname: Wu
authors.forename: Kavirayani R
authors.initials: KR
authors.lastname: Prasad
authors.forename: Danyang
authors.initials: D
authors.lastname: Li
authors.forename: Bin
authors.initials: B
authors.lastname: Yang
authors.forename: Kerisha
authors.initials: K
authors.lastname: Bowen
authors.forename: Seung H
authors.initials: SH
authors.lastname: Lee
authors.forename: John H
authors.initials: JH
authors.lastname: Eardley
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis*; D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000577:Amides; D007659:Ketones; D013454:Sulfoxides