A New Chiral, Cationic β‐Amino Alcohol Equivalent: A Variable Approach to Enantiomerically Pure Building Blocks for Hydroxyethylene Isosters | Zendy

Danielmeier Karsten | Zendy; Schierle Kerstin | Zendy; Steckhan Eberhard | Zendy

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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.

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