Convenient method for the kinetic resolution of β-aminoalcohols

Tetrahedron Letters

Volumn 46, Issue 52, 2005, Pages 9005-9007

  Pelotier, Béatrice ^a,b   Priem, Ghislaine ^a   Macdonald, Simon J F ^a   Anson, Mike S ^a   Upton, Richard J ^a   Campbell, Ian B ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

Aminoalcohols; Enantioselective acylations; Kinetic resolution; Nonenzymatic nucleophilic catalysts; Trifluoroacetamides

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; AMINOALCOHOL; N 4' PYRIDINYL ALPHA METHYLPROLINE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHIRALITY; ENANTIOMER; KINETICS; STEREOCHEMISTRY; TECHNIQUE;

EID: 28244475334     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.111     Document Type: Article

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25. 3CO)-protected (1R,2S)-(+)-cis-1-amino-2-indanol 2f (0.05 mmol) was stirred at room temperature in 1.5 ml of a 2 M ammonia in methanol solution until completion (2 days). Solvent was removed and (1R,2S)-(+)-cis-1-amino-2-indanol was purified on a silica gel column (ethyl acetate then methanol). The optical rotation of recovered alcohol is [ α ] D 20 +62.2 (c 0.4, chloroform). In the literature (99% ee/GLC, Aldrich): [ α ] D 22 +63 (c 0.2, chloroform).