A mild and efficient approach to enantioenriched alpha-hydroxyethyl alpha,beta-unsaturated delta-lactams
- A mild and efficient approach to enantioenriched alpha-hydroxyethyl alpha,beta-unsaturated delta-lactams
- 한서정; Brian M. Stoltz
- Issue Date
- Tetrahedron letters
- VOL 57, NO 21-2235
- A straightforward approach toward enantioenriched a-substituted alpha,beta-unsaturated delta-lactams is described. Although a considerable number of approaches toward alpha,beta-unsaturated S-lactams have been reported, there are relatively few examples of enantioenriched alpha,delta-disubstituted alpha,beta-unsaturated delta-lactams formation. The delta-stereocenter was formed by addition of allylmagnesium bromide to an N-tent-butylsulfinyl imine. The alpha,beta-unsaturated delta-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 alpha-position of the alpha,beta-unsaturated lactam.
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