New zinc(II)-based catalyst for asymmetric azomethine ylide cycloaddition reactions

Date

2006-10-12

Author

Doğan, Özdemir
GARNER, Philip
BULUT, Adnan
Youngs, Wiley J.
PANZNER, Matthew

Metadata

Show full item record

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

Item Usage Stats

90
views

0
downloads

A new chiral aziridino alcohol ligand for zinc(II)-catalyzed azomethine ylide cycloadditions is described. In the presence of this catalyst, N-arylidene glycine methyl esters react with a variety of dipolarophiles to give substituted pyrrolidines in very good to excellent chemical yields and up to 95% ee. The absolute sense of asymmetric induction appears to be dipolarophile-dependent.

Subject Keywords

Physical and Theoretical Chemistry, Organic Chemistry, Biochemistry

URI

https://hdl.handle.net/11511/39889

Journal

ORGANIC LETTERS

DOI

https://doi.org/10.1021/ol061521f

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

A novel one-pot synthesis of ferrocenyl-substituted 1,2,4-oxadiazoles Zora, Metin; Kelgokmen, YILMAZ (Elsevier BV, 2014-06-01) One-pot synthesis of 5-ferrocenyl-1,2,4-oxadiazoles via the reaction between 3-ferrocenylpropynal and amidoximes is described. 3-Ferrocenylpropynal reacts with a variety of amidoximes in the presence of KOH in refluxing dioxane to afford a broad range of 5-ferrocenyl-1,2,4-oxadiazole derivatives. The reaction first produces the corresponding conjugate addition product which, upon cyclization and rearrangement, yields the targeted 1,2,4-oxadiazole. The reaction appears to be general for a diversity of amidox...
Synthesis of ferrocenyl pyrazoles by the reaction of (2-formyl-1-chlorovinyl)ferrocene with hydrazines Zora, Metin (Elsevier BV, 2007-10-15) Synthesis of ferrocenyl-substituted pyrazoles via the reaction between (2-formyl-1-chlorovinyl)ferrocene and hydrazine derivatives is described. Depending upon the substitution pattern of hydrazine, the reaction affords 1-alkyl/aryl-5-ferrocenylpyrazoles and/or 1-alkyl/ aryl-3-ferrocenylpyrazoles. The reaction appears to be general for a variety of hydrazine derivatives.
Synthesis of ferrocenyl pyrazoles by the reaction of 3-ferrocenylpropynal with hydrazinium salts Zora, Metin; Odabasoglu, Mustafa; Bueyuekguengoer, Orhan; Turgut, Guenseli (Elsevier BV, 2008-01-01) Synthesis of ferrocenyl-substituted pyrazoles via the reaction between 3-ferrocenylpropynal and hydrazinium salts is described. Depending upon the substitution pattern of hydrazine derivative, the reaction affords 1-alkyl/aryl-5-ferrocenylpyrazoles and/or 1-alkyl/aryl-3-ferrocenylpyrazoles. Structures of 5-ferrocenyl-1-phenyl-1H-pyrazole, 1-benzyl-5-ferrocenyl-1H-pyrazole and 2-(3-ferrocenylpyrazol-1-yl)ethanol were identified by X-ray crystallography.
A new and efficient chemoenzymatic route to both enantiomers of alpha '-acetoxy and alpha '-hydroxy-alpha-methoxy cyclic enones Demir, Ayhan Sıtkı; Caliskan, Z; Aydin, AE; Bicer, I (Elsevier BV, 2006-03-06) A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy and alpha'-hydroxy-alpha-methoxy cyclic enones starting from alpha-hydroxy cyclic enones is described. Protection of 1,2-diketones, manganese(III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of alpha'-acetoxy enones gives acetoxy enones 3a-d and hydroxy enones 4a-d with high enantiomeric excesses (up to 99%) and good yields. The transesterification of rac-4b in the presence of DMAP af...
Novel enantioselective synthesis of both enantiomers of furan-2-yl Amines and amino acids Demir, Ayhan Sıtkı; Sesemoglu, O; Ulku, D; Arici, C (Wiley, 2003-01-01) A new enantioselective synthesis of furan-2-yl amines and amino acids is described, in which the key step is the oxazaborolidine-catalyzed enantioselective reduction of O-benzyl (E)- and (Z)-furan-2-yl ketone oximes to the corresponding chiral amines. The chirality of the furan-2-yl amines is fully controlled by the appropriate choice of the geometrical isomer of the O-benzyl oxime. Oxidation of the furan ring furnished amino acids in high yields.

Citation Formats

Ö. Doğan, P. GARNER, A. BULUT, W. J. Youngs, and M. PANZNER, “New zinc(II)-based catalyst for asymmetric azomethine ylide cycloaddition reactions,” ORGANIC LETTERS, pp. 4687–4690, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/39889.