Show/Hide Menu
Hide/Show Apps
Logout
Türkçe
Türkçe
Search
Search
Login
Login
OpenMETU
OpenMETU
About
About
Open Science Policy
Open Science Policy
Open Access Guideline
Open Access Guideline
Postgraduate Thesis Guideline
Postgraduate Thesis Guideline
Communities & Collections
Communities & Collections
Help
Help
Frequently Asked Questions
Frequently Asked Questions
Guides
Guides
Thesis submission
Thesis submission
MS without thesis term project submission
MS without thesis term project submission
Publication submission with DOI
Publication submission with DOI
Publication submission
Publication submission
Supporting Information
Supporting Information
General Information
General Information
Copyright, Embargo and License
Copyright, Embargo and License
Contact us
Contact us
Chemoenzymatic synthesis of enantiomerically enriched 2-oxobicyclo[m.1.0]alkan-3-yl acetate derivatives
Date
2006-01-23
Author
ÖZDEMİRHAN, FAZİLET DEVRİM
ÇELİK, MURAT
ATLI, SELİN
Tanyeli, Cihangir
Metadata
Show full item record
This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
.
Item Usage Stats
216
views
0
downloads
Cite This
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.
Subject Keywords
Physical and Theoretical Chemistry
,
Inorganic Chemistry
,
Organic Chemistry
,
Catalysis
URI
https://hdl.handle.net/11511/40329
Journal
TETRAHEDRON-ASYMMETRY
DOI
https://doi.org/10.1016/j.tetasy.2006.01.004
Collections
Department of Chemistry, Article
Suggestions
OpenMETU
Core
Stereoselective synthesis of optically active cyclitol precursors via a chemoenzymatic method
Oguzkaya, Funda; Sahin, Ertan; Tanyeli, Cihangir (Elsevier BV, 2006-11-17)
Racemic alpha'-acetoxy alpha,beta-unsaturated cyclohexanone has been converted to the corresponding enantiomerically enriched alpha'-hydroxylated and acetoxylated compounds with 97% ee via enzymatic resolution with PLE. OSO4-Catalyzed dihydroxylation of enantiomerically enriched alpha'-acetoxylated compound afforded a single diastereomer in 85% chemical yield. The absolute configuration of 2,3,6-triacetoxycylohexanone was determined by X-ray diffraction analysis. Subsequent Luche reduction allowed us to obt...
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...
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...
A bis-Lewis basic 2-aminoDMAP/prolinamide organocatalyst for application to the enantioselective synthesis of Warfarin and derivatives
IŞIK, Murat; Akkoca, H. Ufuk; Akhmedov, I. Mecidoglu; Tanyeli, Cihangir (Elsevier BV, 2016-06-01)
A new chiral sec-amine/amidine-base hybrid catalyst, 2-aminoDMAP/prolinamide, is reported, which is able to catalyze conjugate addition of 4-hydroxycoumarin and various benzylideneacetones, a reaction that directly gives anticoagulant Warfarin and its analogues, with good yields (70-87%) and enantioselectivities (58-72%).
Benzaldehyde lyase-catalyzed enantioselective carboligation of aromatic aldehydes with mono- and dimethoxy acetaldehyde
Demir, Ayhan Sıtkı; Sesenoglu, O; Dunkelmann, P; Muller, M (American Chemical Society (ACS), 2003-06-12)
Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with methoxy and dimethoxy acetaldehyde and furnishes (R)-2-hydroxy-3-methoxy-1-arylpropan-1-one and (R)-2-hydroxy-3,3-dimethoxy-1-arylpropan-1-one in high yields and enantiomeric excess via acyloin linkage. Aromatic aldehydes and benzoins are converted into enamine-carbanion-like intermediates prior to carboligation.
Citation Formats
IEEE
ACM
APA
CHICAGO
MLA
BibTeX
F. D. ÖZDEMİRHAN, M. ÇELİK, S. ATLI, and C. Tanyeli, “Chemoenzymatic synthesis of enantiomerically enriched 2-oxobicyclo[m.1.0]alkan-3-yl acetate derivatives,”
TETRAHEDRON-ASYMMETRY
, pp. 287–291, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/40329.