title: A mild and efficient approach to enantioenriched α-hydroxyethyl α,β-unsaturated δ-lactams.
abstract: A straightforward approach toward enantioenriched α-substituted α,β-unsaturated δ-lactams is described. Although a considerable number of approches toward α,β-unsaturated δ-lactams have been reported, there are relatively few examples of enantioenriched α,δ-disubstituted α,β-unsaturated δ-lactams formation. The δ-stereocenter was formed by addition of allylmagnesium bromide to anN-tert-butylsulfinyl imine. The α,β-unsaturated δ-lactam was furnished by ring-closing metathesis. Although Baylis-Hillman chemistry failed on this cyclic compound, introduction of the hydroxyethyl group prior to ring-closing metathesis was successful. A Baylis-Hillman reaction was used to introduce the substituent at the α-position of the α,β-unsaturated lactam.
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engi neering, California Institute of Technology, 1200 E California Boulevard, MC 101-20, Pasadena, CA 91125, USA.
authors.forename: Seo-Jung
authors.initials: SJ
authors.lastname: Han
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engi neering, California Institute of Technology, 1200 E California Boulevard, MC 101-20, Pasadena, CA 91125, USA.
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
keywords: Asymmetric allylation; Baylis-Hillman reaction; Ring-closing metathesis; δ-Lactams