| Abstract
| - Condensation of allylborane reagents 9 and12 with aldehydes gaveanti-3-[(diphenylmethylene)amino]-1-alken-4-ols 10 and 13 with high relativeand absolute stereocontrol. Subsequentdeprotection gave the corresponding freeanti-3-amino-1-alken-4-ols 11 and 14.Alternatively,reaction of imines 13a, 13f, and 13gwith trifluoromethanesulfonic anhydride and acidicmethanolgave, via rearrangement, double inversion, and hydrolysis,the isomeric anti-4-amino-1-alken-3-ols 22, 38a, and 38b in good yield.The stereochemistry of the rearrangement products hasbeenestablished by a single crystal X-ray study of compound 37and by chemical correlation.
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