1. A mild and efficient approach to enantioenriched α-hydroxyethyl α,β-unsaturated δ-lactams
- Author
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Seo-Jung Han and Brian M. Stoltz
- Subjects
Cyclic compound ,Allylmagnesium bromide ,010405 organic chemistry ,Chemistry ,Stereochemistry ,Organic Chemistry ,Imine ,Substituent ,010402 general chemistry ,Metathesis ,01 natural sciences ,Biochemistry ,Article ,0104 chemical sciences ,chemistry.chemical_compound ,Ring-closing metathesis ,Drug Discovery ,Lactam ,Baylis–Hillman reaction - Abstract
A straightforward approach toward enantioenriched α-substituted α,β-unsaturated δ-lactams is described. Although a considerable number of approaches 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 an N-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. more...
- Published
- 2016
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