176538-16-2Relevant academic research and scientific papers
Convenient asymmetric syntheses of anti-β-amino alochols
Barrett, Anthony G. M.,Seefeld, Mark A.,White, Andrew J. P.,Williams, David J.
, p. 2677 - 2685 (1996)
Condensation of allylborane reagents 9 and 12 with aldehydes gave anti-3-[(diphenylmethylene)-amino]-1-alken-4-ols 10 and 13 with high relative and absolute stereocontrol. Subsequent deprotection gave the corresponding free anti-3-amino-1-alken-4-ols 11 and 14. Alternatively, reaction of imines 13a, 13f, and 13g with trifluoromethanesulfonic anhydride and acidic methanol gave, 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 has been established by a single crystal X-ray study of compound 37 and by chemical correlation.
