title: Facile approach to optically active alpha-alkylidene-beta-amino esters by thermal Overman rearrangement.
abstract: A convenient synthetic method for enantioenriched (E)-alpha-alkylidene-beta-amino esters has been developed through thermal Overman rearrangement. Readily accessible (Z)-beta-branched Morita-Baylis-Hillman esters serve as chiral pool precursors. Thermal rearrangement proceeded through a concerted pseudopericyclic transition state to produce (E)-stereoselective products. We expanded the synthetic utilities of alpha-alkylidene-beta-amino esters via preparation of alpha-alkylidene-beta-lactam derivatives.
authors.affiliation: Department of Chemistry, Sungkyunkwan University, Suwon 440-746, Korea.
authors.forename: Sung Il
authors.initials: SI
authors.lastname: Lee
authors.forename: Soon Young
authors.initials: SY
authors.lastname: Moon
authors.forename: Geum-Sook
authors.initials: GS
authors.lastname: Hwang
authors.forename: Do Hyun
authors.initials: DH
authors.lastname: Ryu