Baker's yeast mediated stereoselective biotransformation of 1-acetoxy-3-aryloxypropan-2-ones

…, A Kolbert, J Bálint, E Fogassy, L Novák, L Poppe

Index: Egri, Gabriella; Kolbert, Attila; Balint, Jozsef; Fogassy, Elemer; Novak, Lajos; Poppe, Laszlo Tetrahedron Asymmetry, 1998 , vol. 9, # 2 p. 271 - 283

Full Text: HTML

Citation Number: 46

Abstract

A series of 1-acetoxy-3-aryloxypropan-2-ones 1a–m were synthesized and subjected to biotransformation by baker's yeast yielding optically active monoacetates 5 or ent-5 and/or diols 4 of moderate to excellent enantiomeric purity. The dependence of the reduction/hydrolysis ratio and stereoselectivity on the size and substitution pattern of the aromatic moiety in the substrate is also discussed.

Related Articles:

Crown cation complex effects. 20. Syntheses and cation binding properties of carbon-pivot lariat ethers

[Dishong, Dennis M.; Diamond, Craig J.; Cinoman, Michael I.; Gokel, Geoge W. Journal of the American Chemical Society, 1983 , vol. 105, # 3 p. 586 - 593]

Heterogeneous Palladium??Catalyzed Synthesis of Aromatic Ethers by Solvent??Free Dehydrogenative Aromatization: Mechanism, Scope, and Limitations Under …

[Sutter, Marc; Lafon, Romain; Raoul, Yann; Metay, Estelle; Lemaire, Marc European Journal of Organic Chemistry, 2013 , # 26 p. 5902 - 5916]

Cyclic sulfites, key intermediates in synthesis of 1-alkylamino-3-aryloxy-2-propanols from glycidol

[Bredikhina; Savel'ev; Bredikhin Russian Journal of Organic Chemistry, 2002 , vol. 38, # 2 p. 213 - 219]

An Unusual (R)??Selective Epoxide Hydrolase with High Activity for Facile Preparation of Enantiopure Glycidyl Ethers

[Zhao, Jing; Chu, Yan-Yan; Li, Ai-Tao; Ju, Xin; Kong, Xu-Dong; Pan, Jiang; Tang, Yun; Xu, Jian-He Advanced Synthesis and Catalysis, 2011 , vol. 353, # 9 p. 1510 - 1518]

One-pot synthesis of aryloxypropanediols from glycerol: towards valuable chemicals from renewable sources

[Truscello, Ada M.; Gambarotti, Cristian; Lauria, Mirvana; Auricchio, Sergio; Leonardi, Gabriella; Shisodia, Suresh U.; Citterio, Attilio Green Chemistry, 2013 , vol. 15, # 3 p. 625 - 628]

More Articles...