Biomaterial Database

Highly enantioselective Ag(i)-catalyzed [3 + 2] cycloaddition of azomethine ylides. 2002

James M Longmire, and Bin Wang, and Xumu Zhang

Department of Chemistry, 152 Davey Laboratory, The Pennsylvania State University, University Park 16802, USA.

A highly reactive Ag(I)-catalyzed [3 + 2] cycloaddition of azomethine ylides is founded using AgOAc as the catalytic precursor and phosphines as ligands. Using a new bis-ferrocenyl amide phosphine (FAP) as the ligand, we found that high enantioselectivities (up to 97% ee) have been achieved in the [3 + 2] cycloaddition of azomethine ylides. Up to four stereogenic centers can be established in this multicomponent coupling reaction from readily available materials such as aldehydes, aminoesters, and dipolarophiles.

UI	MeSH Term	Description	Entries
D008298	Maleates	Derivatives of maleic acid (the structural formula (COO-)-C
D011759	Pyrrolidines	Compounds also known as tetrahydropyridines with general molecular formula (CH2)4NH.	Tetrahydropyridine,Tetrahydropyridines
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D003500	Cyclization	Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Cyclizations
D001391	Azo Compounds	Organic chemicals where aryl or alkyl groups are joined by two nitrogen atoms through a double bond (R-N	Azo Dye,Azo Dyes,Compounds, Azo,Dye, Azo,Dyes, Azo
D012834	Silver	An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer