Abstract
Nine R/S pairs of 2-heteroaromatic-substituted 1,2-amino alcohols were synthesized through
1,2-nucleophilic addition between chiral N-(tert-butylsulfinyl)imines and heteroaromatic carbanions. In most cases, the R
S-isomer of N-(tert-butylsulfinyl)imines afforded the R amino alcohol from deprotection of the major diastereomer, and S
S-imines afforded the S product. In general, this procedure allows for the preparation of a variety of enantiomeric
pairs of 2-heteroaromatic-substituted 1,2-amino alcohols on a practical scale (>10
g) in two steps in good yields.
Key words
amino alcohols - asymmetric synthesis - chiral auxiliaries - heterocycles - stereoselectivity