Chemoenzymatic synthesis of both enantiomers of 2-chloro-1-(2-furyl)ethanol

Gercek, Z
Karakaya, D
Demir, Ayhan Sıtkı
Enzyme catalyzed transesterification of rac-2-chloro-1-(2-furyl)ethanol rac-1 using vinyl acetate afforded the enantiomers of 2-chloro-1-(2-furyl)ethanol 1 and 2-chloro-1-(2-furyl)ethyl acetate 2 in high enantiomeric excess. Several lipases were used for the kinetic resolution of racemic 2-chloro-1-(2-furyl)ethanol l, in which the lipases from Pseudomonas cepacia, Candida antarctica and Candida cylindracea displayed high enantioselectivity towards 1.


Chemoenzymatic synthesis of both enantiomers of 3-hydroxy-2,3-dihydro-4H-chromen-4-one
Demir, AS; Aybey, A; Sesenoglu, O; Polat, Faruk (Elsevier BV, 2003-06-06)
4-Oxo-3,4-dihydro-2-chromen-3-yl acetate is synthesized using manganese(III)acetate starting from 2,3-dihydro-4H-chromen-4-one. K2CO3 mediated hydrolysis of 4-oxo-3,4-dihdro-2-chromen-3-yl acetate furnished 3-hydroxy-2,3-dihydro-4H-chromen-4-one in high yield. The enantioselective hydrolysis of (+/-)-4-oxo-3,4-dihydro-2-chromen-3-yI acetate in various organic solvent-phosphate buffer (pH7) systems and enantioselective transesterification of (+/-)-3-hydroxy-2,3-dihydro-4H-chromen-4-one in organic solvents wa...
Chemoenzymatic synthesis of alpha(1)- and alpha-acetoxylated cyclic ketones
Tanyeli, Cihangir; Akhmedov, M (Elsevier BV, 2004-06-07)
alpha,beta-Unsaturated and saturated cyclic ketones were selectively oxidized at the alpha'- and alpha-positions using Mn(OAc)(3) and Pb(OAc)(4), respectively, resulting in high chemical yields. The resultant racemic alpha'- and alpha-acetoxylated substrates were resolved into corresponding enantiomerically enriched alpha'- and alpha-hydroxylated and acetoxylated compounds with 96-98% ee via PLE hydrolysis. The absolute configurations of alpha'-acetoxy-alpha,beta-unsaturated cyclic ketones were determined b...
Enantioselective synthesis of both enantiomers of 2-amino-2-(2-furyl)ethan-1-ol as a flexible building block for the preparation of serine and azasugars
Demir, Ayhan Sıtkı; Sesenoglu, O; Aksoy-Cam, H; Kaya, H; Aydogan, K (Elsevier BV, 2003-05-16)
The selective conversion of 1-(2-furyl)-2-hydroxyethan-1-one and ethyl 2-(2-furyl)-2-oxo acetate into (E)- and (Z)-oximes and oxime ethers followed by oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2-amino-2-(2-furyl)ethan-1-ol with an ee of up to 96%.
Application of ferrocenyl substituted aziridinylmethanols (FAM) as chiral ligands in enantioselective conjugate addition of diethylzinc to enones
İŞLEYEN, Alper; Doğan, Özdemir (Elsevier BV, 2007-03-30)
Easily available ferrocenyl substituted aziridinylmethanol FAM-4a complexes with nickel and catalyzes the enantioselective diethylzinc addition to various enones with enantiomeric excesses reaching 80%. The ligand can be recovered and used without losing its activity. The sense of induction was found to be dependent on the configuration of the aziridine ring.
Chemoenzymatic synthesis of enantiomerically enriched 2-oxobicyclo[m.1.0]alkan-3-yl acetate derivatives
ÖZDEMİRHAN, FAZİLET DEVRİM; ÇELİK, MURAT; ATLI, SELİN; Tanyeli, Cihangir (Elsevier BV, 2006-01-23)
Racemic alpha'-acetoxy alpha,beta-unsaturated cyclopentanone and cyclohexanone have been resolved into the corresponding enantiomerically enriched alpha'-hydroxylated and acetoxylated compounds with 96-97% ee via PLE hydrolysis. Stereoselectivity in the palladium(II)-catalyzed reaction between the enantiomerically enriched alpha'-acetoxylated compounds and diazomethane has been investigated. In the alpha'-acetoxylated cyclopentenone, preferential cyclopropanation occurs in the anti-form, whereas alpha'-acet...
Citation Formats
Z. Gercek, D. Karakaya, and A. S. Demir, “Chemoenzymatic synthesis of both enantiomers of 2-chloro-1-(2-furyl)ethanol,” TETRAHEDRON-ASYMMETRY, pp. 1743–1746, 2005, Accessed: 00, 2020. [Online]. Available: