Chemoenzymatic synthesis of enantiomerically enriched 2-oxobicyclo[m.1.0]alkan-3-yl acetate derivatives

OZDEMIRHAN, FD; Celik, Murat; ATLI, S; TANYELI, C

doi:10.1016/j.tetasy.2006.01.004

Chemoenzymatic synthesis of enantiomerically enriched 2-oxobicyclo[m.1.0]alkan-3-yl acetate derivatives

OZDEMIRHAN F., Celik M., ATLI S., TANYELI C.

TETRAHEDRON-ASYMMETRY, cilt.17, sa.2, ss.287-291, 2006 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 17 Sayı: 2
Basım Tarihi: 2006
Doi Numarası: 10.1016/j.tetasy.2006.01.004
Dergi Adı: TETRAHEDRON-ASYMMETRY
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.287-291
Atatürk Üniversitesi Adresli: Evet

Özet

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'-acetoxylated cyclohexenone affords both syn- and anti-products (syn:anti, 61:36%). The relative configuration of the products was determined by NOE experiments. (c) 2006 Elsevier Ltd. All rights reserved.