- Some general parameters have been established for nitrone cycloadditions to 2-substituted vinylsilanes. Nitrones and vinylsilanes react to give isoxazolidines with the TMS group at either the C-5 or C-4 position. While 5-TMS isoxazolidines have been fragmented to (alpha),(beta)-unsaturated aldehydes, these isoxazolidines may also be converted into (beta)-amino aldehydes. (beta)-Amido aldehydes were then elaborated into (beta)-amino acids and (beta)-lactams., However, 4-TMS isoxazolidines, which are the predominant regioisomers from the cycloaddition, have been converted to allylic amines via a Peterson elimination methodology with stereospecific control of the double bond geometry. These allylic amines were subsequently converted stereoselectively into (gamma)-lactams via a Cu(I) mediated cyclization., and Nitrones and allyltrimethylsilane produced 5-(trimethylsilylmethyl)isoxazolidines exclusively. Using Peterson elimination methodology, these isoxazolidines were subsequently converted into homoallylic amines.
- Dissertation Note:
- Ph.D. The Pennsylvania State University 1986.
- Source: Dissertation Abstracts International, Volume: 47-04, Section: B, page: 1559.
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