Catalytic enantioselective addition of diethylzinc to aldehydes using aziridine based chiral ligands

Date

2007-05-16

Author

BULUT, Adnan
ASLAN, Ayhan
İZGÜ, Enver Cagri
Doğan, Özdemir

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

200
views

0
downloads

The readily available ferrocenyl substituted aziridinylmethanol 1 (FAM-1) was used as a chiral catalyst in the diethylzinc addition reaction to aromatic and aliphatic aldehydes to give secondary alcohols in high yields and up to 99% enantiomeric excess at room temperature. The catalyst can be recovered and used without losing its activity.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/39220

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2007.04.013

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

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%.
An asymmetric synthesis of both enantiomers of 2,2,2-trifluoro-1-furan-2-yl-ethylamine and 3,3,3-trifluoroalanine from 2,2,2-trifluoro-1-furan-2-yl-ethanone Demir, Ayhan Sıtkı; Sesenoglu, O; Gercek-Arkin, Z (Elsevier BV, 2001-09-13) The selective conversion of 2,2,2-trifluoro-1-furan-2-yl-ethanone into (E)- and (Z)-oximes and oxime ethers and subsequent oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2,2,2-trifluoro-1-furan-2-yl-ethylamine with e.e. of up to 88%. Oxidation of the furan ring afforded both enantiomers of 3,3,3-trifluoroalanine in 91-93% yields.
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...
Amination/annulation of chlorobutenones with chiral amine compounds: synthesis of 1,2,4-trisubstituted pyrroles Demir, Ayhan Sıtkı; Igdir, AC; Gunay, NB (Elsevier BV, 2005-10-03) A series of 1,2,4-trisubstituted pyrroles have been synthesized in 83-96% yields on treatment of chiral primary amines, amino alcohols and esters of alpha-amino acids with different chlorobutenones in benzene-triethylamine. The conversions proceed without racemization.
Asymmetric synthesis of 1,4-amino alcohol ligands with a norbornene backbone for use in the asymmetric diethylzinc addition to benzaldehyde Tanyeli, Cihangir (Elsevier BV, 2005-06-06) The asymmetric synthesis of cis-1,4-amino alcohols with a norbornene backbone was performed starting with (2S,3R)(-)-cis-hemiester 2 (98% ee). Chemoselective amination with NH4OH and HMPTA followed by LAH reduction afforded 5 and 7. respectively. Amido ester 6 was transformed into chiral ligand 9 with Grignard reaction followed by LAH reduction. The chiral ligands 5. 7. and 9 were subjected to asymmetric diethylzinc addition to examine their effectiveness as chiral catalysts. Among these, c chiral ligand 7 ...

Citation Formats

A. BULUT, A. ASLAN, E. C. İZGÜ, and Ö. Doğan, “Catalytic enantioselective addition of diethylzinc to aldehydes using aziridine based chiral ligands,” TETRAHEDRON-ASYMMETRY, pp. 1013–1016, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/39220.