Catalytic asymmetric 1,3-dipolar cycloadditions of azomethine yllides using chiral ferrocenyl substituted aziridinylmethanol (Fam)-zinc complexes

2005-08-28
Doğan, Özdemir
Koyuncu, H
Bulut, A

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In recent years one-pot reactions have been studied significiantly by different research groups. These reactions provide complex molecules from very simple starting materials in a single step. For that reason it is considered as atom economical reaction and “green chemistry”. Asymmetric versions of these reactions are also being studied by organic groups for the synthesis of complex chiral compounds. In this respect, we have studied metal catalyzed one-pot reaction of azomethine ylides with electron deffici...
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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.
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The first catalytic intermolecular aldehyde-ketone coupling via acyl phosphonate is reported. Acyl phosphonates are potent acyl anion precursors, which generate acyl anion equivalents under the influence of cyanide anion via phosphonate-phosphate rearrangement. These anions readily react with activated ketones to form acyloin type coupling in 41-95% yields.
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Ferrocenyl-substituted aziridinylmethanol (Fam-1) was used as a catalyst with zinc for the asymmetric nitroaldol (Henry) reaction. This catalyst worked with a variety of aldehydes (aromatic, aliphatic, alpha,beta-unsaturated, and heteroaromatic) and alpha-ketoesters to give the nitroaldol product in up to 97% yield and 91% ee. The chiral ligand call be recovered and recycled Without losing its activity.
Citation Formats
Ö. Doğan, H. Koyuncu, and A. Bulut, “Catalytic asymmetric 1,3-dipolar cycloadditions of azomethine yllides using chiral ferrocenyl substituted aziridinylmethanol (Fam)-zinc complexes,” 2005, vol. 230, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/53110.