X=Y−ZH compounds as potential 1,3-dipoles. Part 43. Metal ion catalysed asymmetric 1,3-dipolar cycloaddition reactions of imines and menthyl acrylate
In: Tetrahedron, Jg. 51 (1995), S. 273-294
Online
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Zugriff:
Metallo-azomethine ylides, generated from imines by the action of amine bases in combination with LiBr or AgOAc, undergo cycloaddition with both 1R, 2S, 5R- and 1S, 2R, 5S-menthyl acrylate at room temperature to give homochiral pyrrolidines in excellent yield. The stronger the base the faster the cycloaddition and the greater the yield with: 2- 2-t-butyl-1,1,3,3-tetramethylguanidine > DBU > NEt 3 . X-Ray crystal structures of representative cycloadducts establish that the absolute configuration of the newly established pyrrolidine stereocentres is independent of the metal salt and the size of the pyrrolidineC(2)-substituent for a series of aryl and aliphatic imines.
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X=Y−ZH compounds as potential 1,3-dipoles. Part 43. Metal ion catalysed asymmetric 1,3-dipolar cycloaddition reactions of imines and menthyl acrylate
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Autor/in / Beteiligte Person: | Stevenson, Paul J. ; Malone, John F. ; Montgomery, John ; Hargreaves, Simon ; Dorrity, Michael R. J. ; Grigg, Ronald ; Barr, Darrin A. ; Thornton-Pett, Mark ; Redpath, James |
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Zeitschrift: | Tetrahedron, Jg. 51 (1995), S. 273-294 |
Veröffentlichung: | Elsevier BV, 1995 |
Medientyp: | unknown |
ISSN: | 0040-4020 (print) |
DOI: | 10.1016/0040-4020(94)00940-v |
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