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Synthesis of ( R )‐ tert ‐Leucinol by Classical Resolution of the Racemic Mixture
Author(s) -
Drauz Karlheinz,
Jahn Wilfried,
Schwarm Michael
Publication year - 1995
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19950010807
Subject(s) - enantiomer , resolution (logic) , block (permutation group theory) , transformation (genetics) , chemistry , stereochemistry , optically active , enantiomeric excess , combinatorial chemistry , leucine , amino acid , enantioselective synthesis , mathematics , organic chemistry , computer science , combinatorics , biochemistry , catalysis , artificial intelligence , gene
Optically active tert ‐leucinol is an important building block in asymmetric synthesis. However, the ( R ) enantiomer particularly has so far remained difficult to obtain, mainly because of the laborious synthesis of the precursor amino acid, ( R )‐ tert ‐leucine. Here we present a new, classical resolution of racemic tert ‐leucinol, which allows straightforward preparation of each, but especially the ( R ) enantiomer, in good yields and high optical purities. The feasibility of the synthesis of useful derivatives is demonstrated by transformation into the corresponding ( R )‐4‐ tert ‐butyl‐2‐oxazolidinone.