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Electrogenerated Chiral 4‐Methoxy‐2‐oxazolidinones as Diastereoselective Amidoalkylation Reagents for the Synthesis of β‐Amino Alcohol Precursors
Author(s) -
SchierleArndt Kerstin,
Kolter Doris,
Danielmeier Karsten,
Steckhan Eberhard
Publication year - 2001
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 - 10.1002/1099-0690(200107)2001:13<2425::aid-ejoc2425>3.0.co;2-2
Subject(s) - enantiopure drug , chemistry , substituent , alcohol , reagent , enantioselective synthesis , nucleophile , molecule , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
A flexible and efficient synthesis of enantiomerically pure 4,5‐substituted 2‐oxazolidinones − important target molecules as precursors of pharmacologically active 2‐oxazolidinones, β‐amino alcohols, β‐blockers and azasugar derivatives − is described. As starting materials, the enantiopure storage forms of chiral N ‐acyliminium ions (4 RS ,5 S )‐5‐chloromethyl‐4‐methoxy‐1,3‐oxazolidin‐2‐one ( 2 ) and (4 RS ,5 R )‐4‐methoxy‐5‐methyl‐1,3‐oxazolidin‐2‐one ( 3 ) were used; these are readily available from the chiral pool with the aid of electrochemical transformations. Substitution of the 4‐methoxy group in building blocks 2 and 3 with a large variety of organometallic nucleophiles resulted in the trans ‐diastereoselective formation of enantiopure 4,5‐disubstituted 2‐oxazolidinones, with a high degree of flexibility in the substituent at the 4‐position.