Practical, highly enantioselective chemoenzymatic one-pot synthesis of short-chain aliphatic β-amino acid esters

Synlett

Volumn , Issue 8, 2009, Pages 1251-1254

  Weiß, Markus ^a   Gröger, Harald ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Amino acids; Aminolysis; Asymmetric catalysis; Enzyme catalysis; Stereoselective synthesis

Indexed keywords

BETA AMINO ACID; ESTER DERIVATIVE; SOLVENT; TRIACYLGLYCEROL LIPASE;

AMINOLYSIS; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; ENANTIOSELECTIVITY; MICHAEL ADDITION; ONE POT SYNTHESIS;

EID: 67649336819     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1216721     Document Type: Article

References (33)

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26. The yields given in Scheme 2 are 'crude yields' since the products have not been isolated.
27. This result is in accordance with previous reports by Berglund et al. showing a nonenenatioselective course of another type of CAL-B-catalyzed Michael addition, see ref. 8.
28. 3 (compounds 3c, 4b). The absolute configuration of 3a was assigned according to the direction of optical rotation of the product 6 after derivatization (see Scheme 3) and its comparison with the literature value given in ref. 12. The absolute configuration of the other esters 3b,c,e has been assigned in analogy to the result in case of 3a. The spectral data of the ester products (S)-3a-c, (R)-3e were in accordance with literature data. The amides 4a-c,e have been fully characterized (data will be published elsewhere).
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31. For the enzymatic resolution of rac-3a with benzylamine as amine and lipase CAL-B as biocatalyst under solvent free conditions at 60°C, an E value of 27 has been obtained for this aminolysis reaction (data not shown).
32. 2O).
33. During completion of our manuscript we became aware of the following publication, describing processes related to our synthesis shown in Scheme 2: Priego, J.; Ortiz-Nava, C.; Carillo-Morales, M.; Lopez-Munguia, A.; Escalante, J.; Castillo, E. Tetrahedron 2009, 65, 536.