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Regiochemistry and stereochemistry of oxirane ring-opening with silyl halides

โœ Scribed by Michael R. Detty; Mark D. Seidler

Book ID
104220890
Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
289 KB
Volume
23
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The ring-opening of various styrene and stilbene oxides with silyl halides was examined. The regiochemistry of ring-opening was independent of the silyl halide used, but the stereochemistry of ring-opening was sensitive to both the choice of halide and the steric bulk of groups attached to silicon.

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Stereo- and regioselective ring opening
Stereo- and regioselective ring opening of alkenyl aziridines with metal halides
โœ Giuliana Righi; Claudia Potini; Paolo Bovicelli ๐Ÿ“‚ Article ๐Ÿ“… 2002 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 138 KB

The reaction of N-Boc-alkenyl aziridines with lithium halides in presence of Amberlyst 15 afforded the stereo-and regioselective ring-opened products in high yields. The following treatment of the bromo-and iododerivatives with silica gel produced the corresponding oxazolidin-2-ones.