Synthesis of Enantiomerically Pure 2-Heteroaromatic-Substituted 1,2-Amino Alcohols from Chiral tert-Butanesulfinyl Aldimines

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

• References

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