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A New Chiral, Cationic β‐Amino Alcohol Equivalent: A Variable Approach to Enantiomerically Pure Building Blocks for Hydroxyethylene Isosters
Author(s) -
Danielmeier Karsten,
Schierle Kerstin,
Steckhan Eberhard
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199622471
Subject(s) - cationic polymerization , alcohol , reagent , chemistry , nucleophile , chiral auxiliary , peptidomimetic , stereochemistry , organic chemistry , medicinal chemistry , enantioselective synthesis , catalysis , peptide , biochemistry
Anodic oxidation of (5S)‐ and (5R)‐ 2 provides (4RS,5S)‐ and (4RS,5R)‐5‐chloromethyl‐4‐methoxyoxazolidin‐2‐one 3 , respectively, in good yields. These are chiral cationic amidoalkylation reagents and, through diastereoselective nucleophilic methoxy group exchange, afford variably functionalized enantiomerically pure amino alcohols 4 as well as 1‐substituted 2,3‐epoxypropylamines 1 , which are precursors for peptidomimetics.