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Synthesis of Enantiopure o ‐Hydroxybenzylamines by Stereoselective Reduction of 2‐Imidoylphenols: Application in the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes
Author(s) -
Palmieri Gianni
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199904)1999:4<805::aid-ejoc805>3.0.co;2-r
Subject(s) - diethylzinc , enantioselective synthesis , enantiopure drug , chemistry , stereoselectivity , catalysis , enantiomer , organic chemistry , combinatorial chemistry , stereochemistry
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 .