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Synthesis of epimeric pure spiro N,S‐acetals of L ‐menthone
Author(s) -
Altenbach HansJosef,
Roth Peter R.,
Brauer David J.
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199508193
Subject(s) - menthone , chemistry , stereochemistry , organic chemistry , menthol
By acetalisation of L ‐menthone (2) with mercaptoacetic acid and derivatives of benzylamine, the spirocyclic N,S‐acetals 3 were obtained as single diastereomers. The reaction of an epimeric mixture of unsubstituted thiazolidinones 4 with acetic anhydride or allyl iodide afforded homochiral N ‐acetyl (5) or N ‐allyl N,S‐acetals (6) , respectively. The configuration of the new stereogenic centres were proven by X‐ray crystallography.
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