Efficient access to enantiomerically pure cyclic α-amino esters through a lipase-catalyzed kinetic resolution

Tetrahedron Asymmetry

Volumn 19, Issue 14, 2008, Pages 1714-1719

  Alatorre Santamaría, Sergio ^a   Rodriguez Mata, María ^a   Gotor Fernández, Vicente ^a   de Mattos, Marcos Carlos ^b   Sayago, Francisco J ^c   Jiménez, Ana I ^c   Cativiela, Carlos ^c   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

^b FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

^c UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHOXYPHENYL ALLYL CARBONATE; ALPHA AMINO ESTER; BENZYL OCTAHYDROINDOLE 2 CARBOXYLATE; CARBONIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIALLYL CARBONATE; ESTER DERIVATIVE; METHYL INDOLINE 2 CARBOXYLATE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA ANTARCTICA; CARBONYLATION; CATALYSIS; ENANTIOMER; ENZYME ACTIVITY; KINETICS; OPTICAL RESOLUTION; PRIORITY JOURNAL;

EID: 48349091261     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.06.010     Document Type: Article

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48. 3-Methoxyphenyl allyl carbonate was prepared following the protocol described in Ref. 4j.
49. See Section 4 for elution conditions.
50. HPLC retention times: (2R,3aR,7aR)-8b, 8.1 min; (2S,3aS,7aS)-8b, 13.3 min. Conditions: 25 × 0.46 cm ID Chiralpak IA column; eluent n-hexane/2-propanol (95:5) at 0.8 mL/min flow rate.
51. Three years ago, some companies commercialized CAL-A in different immobilized supports as, for example, Biocatalytics or Roche. Nowadays, this enzyme is not available from Roche any more. On the other hand, after Biocatalytics was purchased by Codexis on July 2007, this immobilized enzyme is produced in a different form.
52. Carbamates 3 and 7a are given as examples of the numerical locants used for NMR assignment.{A figure is presented}.