Publication detail

Regio- and stereoselective cycloadditions of (1Z,4R*,5R*)-1-arylmethylidene-4-benzoylamino-3-oxo-5-phenylpyrazolidin-1-ium-2-ides to methyl methacrylate

Year: 2011

Type of publication: článek v odborném periodiku

Name of source: Tetrahedron

Publisher name: Pergamon-Elsevier Science Ltd.

Place: Oxford

Page from-to: 9729-9735

Titles:

Language	Name	Abstract	Keywords
cze	Regio- a stereoselektivní cykloadice (1Z,4R,5R)-1-arylmethyliden-4-benzoylamino-3-oxo-5-fenylpyrazolidin-1-ium-2-idů na methyl-methakrylát	[3+2] Cykloadice (1Z,4R,5R)-1-arylmethyliden-4-benzoylamino-3-oxo-5-fenylpyrazolidin-1-ium-2-idů 1a–e na methyl-methakrylát poskytla exkluzivně 1-CO2Me regioisomery 3/3′, v 1–67% výtěžku. Stereokontrola byla závislá na ortho-substituentu na 1′-aryl skupině v dipolu 1: ortho-nesubstituované dipoly 1a–c poskytly jako hlavní isomery (1R,3R,5R,6R) 3a–c, kdežto ortho-disubstituované dipoly poskytly jako hlavní isomery (1R,3S,5R,6R)-3′d,e. Struktury cykloaduktů byly určeny s pomocí NMR a X-ray difrakce.	stereoselektivní cykloadice;NMR;pyrazolidin;[3+2] Cykloadice
eng	Regio- and stereoselective cycloadditions of (1Z,4R,5R)-1-arylmethylidene-4-benzoylamino-3-oxo-5-phenylpyrazolidin-1-ium-2-ides to methyl methacrylate	[3+2] Cycloadditions of (1Z,4R,5R)-1-arylmethylidene-4-benzoylamino-3-oxo-5-phenylpyrazolidin-1-ium-2-ides 1a–e to methyl methacrylate gave the 1-CO2Me regioisomers 3/3′, exclusively, in 1–67% yields. Stereocontrol was dependent on the ortho-substituents at the 1′-aryl group in dipole 1: ortho-unsubstituted dipoles 1a–c gave the major (1R,3R,5R,6R)-isomers 3a–c, whilst ortho-disubstituted dipoles gave the major (1R,3S,5R,6R)-isomers 3′d,e. The structures of cycloadducts were determined by NMR and X-ray diffraction.	Azomethine imines;[3+2] Cycloaddition;NMR;Pyrazolidinones;Stereoselective synthesis

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