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

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

doi:10.1016/j.tetasy.2006.01.004

Makale Tam Makale Uluslararası 2006

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

FD OZDEMIRHAN, Murat Çelik, S ATLI, C TANYELI

TETRAHEDRON-ASYMMETRY Cilt 17 · Sayı 2 · ss. 287–291 · 23.01.2006

DOI ile aç

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.

Atıf için künye

OZDEMIRHAN, F., Çelik, M., ATLI, S., & TANYELI, C. (2006). Chemoenzymatic synthesis of enantiomerically enriched 2-oxobicyclo[m.1.0]alkan-3-yl acetate derivatives. TETRAHEDRON-ASYMMETRY, 17(2), 287–291. https://doi.org/10.1016/j.tetasy.2006.01.004

BibTeX

@article{ozdemirhan2006-71785,
  author = {OZDEMIRHAN, FD and Çelik, Murat and ATLI, S and TANYELI, C},
  title = {Chemoenzymatic synthesis of enantiomerically enriched 2-oxobicyclo[m.1.0]alkan-3-yl acetate derivatives},
  journal = {TETRAHEDRON-ASYMMETRY},
  year = {2006},
  volume = {17},
  number = {2},
  pages = {287--291},
  issn = {0957-4166},
  doi = {10.1016/j.tetasy.2006.01.004},
  url = {https://akademik.atauni.edu.tr/yayinlar/71785-chemoenzymatic-synthesis-of-enantiomerically-enriched-2-oxobicyclom10alkan-3-yl}
}