Synthesis of Enantiopure o‐Hydroxybenzylamines by Stereoselective Reduction of 2‐Imidoylphenols: Application in the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes
摘要:
Enantiopure o-hydroxybenzylamines 2a-i were synthesized by diastereoselective reduction of the 2-imidoylphenols (R)-1a-i. Conformational analysis enabled the assignment of the absolute configurations of compounds 2a-i. The accessible o-hydroxybenzylamine (R,R)-2h serves as an effective catalyst precursor for highly enantioselective addition of diethylzinc to aliphatic and aromatic aldehydes. This pathway represents a practical and operationally very simple methodology for the enantioselective synthesis of both the enantiomers of secondary alcohols 7a-f.
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DOI:
10.1002/(SICI)1099-0690(199904)1999:4<805::AID-EJOC805>3.0.CO;2-
被引量:
年份:
2010
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