title: Convenient Asymmetric Syntheses of anti-beta-Amino Alcohols.
abstract: 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.
authors.affiliation: Imperial College of Science, Technology & Medicine, London SW7 2AY, England.
authors.forename: Anthony G. M.
authors.initials: AG
authors.lastname: Barrett
authors.forename: Mark A.
authors.initials: MA
authors.lastname: Seefeld
authors.forename: Andrew J. P.
authors.initials: AJ
authors.lastname: White
authors.forename: David J.
authors.initials: DJ
authors.lastname: Williams