Highly stereoselective syntheses of syn- and anti-1,2-amino alcohols.
The reduction of N-protected amino ketones can be carried stereoselectively to produce either the syn- or anti-amino alcohol diastereomer. Carbamate-protected amino ketones can be reduced predictably and selectively to anti-amino alcohols with LiAlH(O-t-Bu)3 in ethanol at -78 degrees C. N-Trityl-protected amino ketones can be reduced selectively to syn-amino alcohols with LiAlH(O-t-Bu)3 in THF at -5 degrees C.
Hoffman
Robert V
RV
Department of Chemistry and Biochemistry, North Horseshoe Drive, New Mexico State University, Las Cruces, New Mexico 88003-8001, USA. rhoffman@nmsu.edu
Maslouh
Najib
N
Cervantes-Lee
Francisco
F