ChemInform Abstract: Kinetic Resolution of β-Alkenyl-, β-Alkynyl- and β-Flavenyl-Substituted...
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ChemInform 2009, 40, issue 01 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.cheminform.wiley-vch.de Stereochemistry O 0030 Kinetic Resolution of β-Alkenyl-, β-Alkynyl- and β-Flavenyl-Substituted β-Hydroxy Esters in Asymmetric Dehydration. — The kinetic resolution of the β-hydroxy esters (II), (IV), (VI) and (VIII) is smoothly achieved by asymmetric dehy- dration using a chiral prolinol-derived diamine ligand (I) in the presence of organozinc reagent. The reaction is limited to α-unsaturated β-hydroxy esters bearing a conjugated β-substituent. Enantioselectivities of up to 98% e.e. can be achieved. In the case of flavenyl-substituted β-hydroxy esters, both the dehydrated product as well as the re- maining enantiomer can be isolated. — (LEE, M. H.; CHOI, E. T.; KIM, D.; LEE, Y. M.; PARK*, Y. S.; Eur. J. Org. Chem. 2008, 33, 5630-5637; Dep. Chem., Konkuk Univ., Seoul 143-701, S. Korea; Eng.) — Mischke 12- 026
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Transcript of ChemInform Abstract: Kinetic Resolution of β-Alkenyl-, β-Alkynyl- and β-Flavenyl-Substituted...
www.cheminform.wiley-vch.de
StereochemistryO 0030 Kinetic Resolution of β-Alkenyl-, β-Alkynyl- and β-Flavenyl-Substituted
β-Hydroxy Esters in Asymmetric Dehydration. — The kinetic resolution of the β-hydroxy esters (II), (IV), (VI) and (VIII) is smoothly achieved by asymmetric dehy-dration using a chiral prolinol-derived diamine ligand (I) in the presence of organozinc reagent. The reaction is limited to α-unsaturated β-hydroxy esters bearing a conjugated β-substituent. Enantioselectivities of up to 98% e.e. can be achieved. In the case of flavenyl-substituted β-hydroxy esters, both the dehydrated product as well as the re-maining enantiomer can be isolated. — (LEE, M. H.; CHOI, E. T.; KIM, D.; LEE, Y. M.; PARK*, Y. S.; Eur. J. Org. Chem. 2008, 33, 5630-5637; Dep. Chem., Konkuk Univ., Seoul 143-701, S. Korea; Eng.) — Mischke
12- 026
ChemInform 2009, 40, issue 01 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cheminform.wiley-vch.de
ChemInform 2009, 40, issue 01 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
