Enantiopure 1,5-diols from dynamic kinetic asymmetric transformation. useful synthetic intermediates for the preparation of chiral heterocycles

Organic Letters

Volumn 10, Issue 10, 2008, Pages 2027-2030

  Leijondahl, Karin ^a   Borén, Linnéa ^a   Braun, Roland ^a   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; HETEROCYCLIC COMPOUND; LIPASE B, CANDIDA ANTARCTICA; RUTHENIUM; TRIACYLGLYCEROL LIPASE;

ARTICLE; BURKHOLDERIA CEPACIA; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; KINETICS; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; BURKHOLDERIA CEPACIA; CATALYSIS; HETEROCYCLIC COMPOUNDS; KINETICS; LIPASE; MOLECULAR STRUCTURE; RUTHENIUM; STEREOISOMERISM;

EID: 47049098712     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800468h     Document Type: Article

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29. The reaction was performed on a 1 mmol scale using 30 mg of PS-C II, 3 equiv of p-ClPhOAc as acyl donor in 5 mL of toluene at 60 °C for 48 h, yielding monoacetate (2R,6R)-2a in 41% yield and 96% de.
30. A control experiment was run without any enzyme present which gave no detectable amount of diacetate ruling out the potential problem with chemical acylation taking place in the reaction.