Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 8, Pages 3740-3753Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo300002u
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- IIT-Kanpur
- CSIR, India
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Lewis acid catalyzed quaternary ammonium salt mediated highly regioselective ring-opening of chiral activated aziridines and azetidines with alcohols to nonracemic beta- and gamma-amino ethers has been developed. The reaction mainly proceeds via an S(N)2 pathway, and the partial racemization of the starting substrate was effectively controlled by using quaternary ammonium salts. beta- and gamma-amino ethers are obtained with high enantio- and diastereospecificity (ee up to >99%, de up to 99%). The methodology was further extended to synthesize morpholines and their homologues with high enantiospecificity (ee up to 90%) when halo alcohols were employed as the nucleophiles.
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