Simple access to novel azetidine-containing conformationally restricted amino acids by chemoselective reduction of β-lactams

Tetrahedron Letters

Volumn 45, Issue 10, 2004, Pages 2193-2196

  Gerona Navarro, Guillermo ^a   Bonache, Ma Angeles ^a   Alías, Miriam ^b   Pérez De Vega, Ma Jesús ^a   García López, Ma Teresa ^a   López, Pilar ^b   Cativiela, Carlos ^b   González Muñiz, Rosario ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b CSIC   (Spain)

Author keywords

Azetidines; Chemoselective reduction; Chiral HPLC; Resolution; Restricted amino acids; Lactams

Indexed keywords

AMINO ACID; AZETIDINE DERIVATIVE; BENZYL DERIVATIVE; BETA LACTAM; PHENYLALANINE; RHODIUM DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; REDUCTION KINETICS; STEREOCHEMISTRY;

EID: 1242272913     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.023     Document Type: Article

References (32)

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22. +.
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27. Preparative resolution of 1d was carried out on a 150 × 20 mm ID column containing the same CSP as analytical column, 10-undecenoate/3,5- dimethylphenylcarbamate of cellulose covalently linked to allyl silica gel. Although chloroform had led to a lower resolution factor, elution was performed in a mixture of n-hexane/2-propanol/chloroform 96:2:2 to increase the sample solubility and, then, the column loadability. Flow rate: 15 mL/min. UV detection: 254 nm.
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30. 3 and each run (0.2 mL) was collected into three separated fractions. The first combined fraction (245 mg) and the last one (335 mg) contained mainly one of the enantiomers (85% and 92% of enantiomeric purity, respectively). The third fraction (400 mg) was reinjected and similar enantioselectives mixtures were obtained. Crystallization of the enriched mixtures in ethanol/hexanes led to the optically pure compounds. By this procedure 275 and 285 mg of the first and second eluted enantiomers of 1d can be obtained.
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32. Polarimetry data of (S)- and (R)-6d , prepared according to the HPLC resolution procedure described here, are higher than those reported in Ref. 20, indicating a more accurate resolution in this case.