The Stereospecific Cyclization of A Threo α-Benzamide Alcohol to A Cis N-Acyl Aziridine

References

• Schaeffer , H. J. and Schwender , C. K. 1974 . J. Med. Chem. , 17 : 6
   PubMed Web of Science ®Google Scholar
• Frump , J. A. 1971 . 483 , : 71
   Google Scholar
• Roush , D. M. and Patel , M. M. 1985 . Syn. Comm. , 15 ( 8 ) : 675
   Web of Science ®Google Scholar
• Mitsunobu , O. 1981 . Synthesis , 1
   Google Scholar
• Johnson , W. S. and Schubert , E. N. 1950 . J. Amer. Chem. Soc , 72 : 2187
   Google Scholar
• Okada , I. , Ichimura , K. and Sado , R. 1970 . Bull. Chem. Soc. Japan , 43 : 1185
   Web of Science ®Google Scholar
• Foglia , T. A. and Gregory , L. M. 1970 . J. Org. Chem. , 35 : 3779 Partial 1H NMR data for 6a: 4.29 (m, H-C-N, 1H), 5.13 (m, H-C-O,1H). For 6b: 4.75 (m, H-C-N, 1H), 5.64 (m, H-C-O,1H). This data is analogous to that reported for symmetrical 2-oxazolines, see
   Google Scholar
• Bose , A. K. , Manhas , M. S. and Sahu , D. P. 1984 . Can. J. Chem. , 62 : 2498 There is precedent in the literature for the formation of an acyl aziridine from a similar substrate, see, Depending on the substitution pattern of L-threonine amides, 8, treatment with triphenylphosphine and diethyl azodicarboxylate can conceivably lead to three, four or five membered rings and acyclic products. Bose has shown that while 8a gave a four membered ring and 8c a 1:1 mixture of four and three membered rings, 8b provided only a cis N-acyl aziridine
   Web of Science ®Google Scholar