Photochemical reaction between tertiary allylic amines and chromium carbene complexes: Synthesis of lactams via a zwitterion aza cope rearrangement

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2871-2876

  Deur, Christopher J ^a   Miller, Michael W ^a   Hegedus, Louis S ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001080877     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951829c     Document Type: Article

References (37)

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11. (a) Diederich, M.; Nubbemeyer, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1026. For related aza Claisen rearrangements of zwittenonic intermediates derived from the addition of tertiary allylic amines to propiolate esters see:
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14. (c) Vedejs, E.; Gingras, M. J. Am. Chem. Soc. 1994, 116, 579 and references therein. For Lewis acid-promoted 3-aza Cope rearrangements of N-alkyl-N-allyl enamines see: Cook, G. R.; Stille, J. R. Tetrahedron 1994, 50, 4105.
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22. This material is synthesized from L-proline, see Experimental Section.
23. This was a major problem in the synthesis of β-lactones, which required Lewis acid catalysis, see reference 14.
24. 53Cr chemical shifts for complexes 1a-e respectively are: 1a δ 187; 1b δ 204; 1c δ 123; 1d δ 82; 1e δ 135.
25. 19F-NMR spectrum of this material to that derived from racemic 2.
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