Fam-Ti catalyzed enantioselective alkynylation of aldehydes

Date

2007-08-16

Author

KOYUNCU, Hasan
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

227
views

0
downloads

Ferrocenyl-substituted aziridinylmethanol (Fam-1) has been used as a chiral catalyst with titanium for enantioselective alkynylation of aromatic, heteroaromatic, aliphatic, and alpha,beta-unsaturated aldehydes to give the corresponding propargylic alcohols in up to 96% yield and 96% ee. The ligand can be prepared easily and recycled.

Subject Keywords

Physical and Theoretical Chemistry, Organic Chemistry, Biochemistry

URI

https://hdl.handle.net/11511/40718

Journal

ORGANIC LETTERS

DOI

https://doi.org/10.1021/ol701535y

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Fam-zinc catalyzed asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides and Koyuncu, Hasan; Doğan, Özdemir; Department of Chemistry (2007) In the first part of this study, four new chiral ligands (FAM) were synthesized and used in catalytic amounts in asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides. This method leads to the synthesis of chiral pyrrolidines, which are found in the structure of many biologically active natural compounds and drugs. It was found that using 10 mol% of one of these chiral ligands with different dipolarophiles (dimethyl maleate, dimethyl fumarate, methyl acrylate, tert-butyl acrylate, and Nmethylm...
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.
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%.
Functionalization of oxabenzonorbornadiene: Manganese(III)-mediated oxidative addition of dimedone ÇALIŞKAN, Raşit; Sari, Ozlem; Balcı, Metin (Wiley, 2017-09-01) 3-Chloro-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-2-yl)-3-hydroxy-5,5-dimethylcy-clohex- 2-en-1-one, synthesized by the reaction of oxabenzonorbornadiene with Mn(OAc)(3) and dimedone in the presence of HCl in acetic acid, was submitted to ring-opening reactions with BBr3 and H2SO4. Reaction with BBr3 yielded 2 products, a 5-membered ring and an 8-membered ring, with the former being the major product. However, the H2SO4-supported reaction exclusively formed an 8-membered ring. The mechanism of formation of th...
Organosilanols as Catalysts in Asymmetric Aryl Transfer Reactions Özçubukçu, Salih; BOLM, Carsten (American Chemical Society (ACS), 2005-03-01) Various ferrocene-based organosilanols have been synthesized in four steps starting from achiral ferrocene carboxylic acid. Applying these novel planar-chiral ferrocenes as catalysts in asymmetric phenyl transfer reactions to substituted benzaldehydes afforded products with high enantiomeric excesses. The best result (91% ee) was achieved in the addition to p-chlorobenzaldehyde with organosilanol 2b, which has a tert-butyl substituent on the oxazoline ring and an isopropyl group on the silanol fragment.

Citation Formats

H. KOYUNCU and Ö. Doğan, “Fam-Ti catalyzed enantioselective alkynylation of aldehydes,” ORGANIC LETTERS, pp. 3477–3479, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/40718.