Synthesis of C₂-Symmetric Chiral Amino Alcohols: Their Usage as Organocatalysts for Enantioselective Opening of Epoxide Ring

Abstract

A series of β-amino alcohols derivatives were synthesized from (R)-2-amino-1-butanol and (S)-1,2-propanediol, and they have been used as organocatalaysts in the racemic ring opening of epoxide in good yields with high enantiomeric excess (up to 97%).

Keywords:

• Asymmetric ring opening
• chiral amino alcohol
• epoxide
• organo catalysis

ACKNOWLEDGMENT

We thank the Scientific and Technological Research Council of Turkey (TUBİTAK) for their financial support (Project No. 107 T 079).

Notes

^a Isolated yield by preparative TLC.

^b Determined by HPLC analysis on a Chiralcel OD-H column.

^c Absolute configuration was determined by comparison of HPLC retention times with those of products of chiral molecules.