Tandem enantioselective organo- and biocatalysis: A direct entry for the synthesis of enantiomerically pure aldols

Tetrahedron Letters

Volumn 45, Issue 41, 2004, Pages 7697-7701

  Edin, Michaela ^a   Bäckvall, Jan E ^a   Córdova, Armando ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Aldol; Catalysis; Kinetic resolutions; Lipase; Proline

Indexed keywords

ALCOHOL DERIVATIVE; KETONE DERIVATIVE; PROLINE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME KINETICS; RACEMIC MIXTURE; REACTION ANALYSIS; STANDARD; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 4544343483     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.079     Document Type: Article

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63. 4) and evaporated. Flash chromatography of the residue furnished hydroxy ketone 1c (0.124 g, 79%) with 77% ee as determined by chiral-phase HPLC analysis. Next, to a stirred mixture of hydroxy ketone 1c (38 mg, 0.182 mmol) and 4 Å molecular sieves in vinyl acetate (1 mL) was added PS-C Amano I (45 mg). The flask was evacuated and filled with argon three times before it was closed and the reaction left to stir at rt for 12 h to furnish acetate 2c in 76% yield with ee >99% as determined by chiral-phase HPLC analysis. No trace of the elimination product was detected by NMR or HPLC analyses
64. The direct addition of vinyl acetate to the reaction mixture containing acetone significantly decreased the lipase-catalyzed kinetic resolution step
65. 4) and evaporated and the residue purified by silica-gel column chromatography to provide hydroxy ketone ent-1c in 51% yield (0.11 g) with >99% ee