DIASTEREOSELECTIVE SYNTHESIS OF TRANS-4,5-DISUBSTITUTED OXAZOLIDIN-2-ONES AND VICINAL AMINO ALCOHOLS THROUGH ALKYLATION OF N-ACYLIMINIUM ION INTERMEDIATES

Article abstract of DOI:10.3987/R-1987-02-0373

Treatment of 5-substituted 4-ethoxyoxazolidin-2-ones (10a-f, 13a,b) with allyltrimethylsilane in the presence of titanium tetrachloride gave the corresponding trans-4,5-disubstituted oxazolidin-2-ones (14a-f, 16a,b), respectively, with high diastereoselectivity.Methallylation of 13a,b with methallyltrimethylsilane yielded 16c,d, respectively.Ring cleavage of 14a-f afforded the corresponding threo vicinal amino alcohols 17a-f, respectively.