Stereodivergent synthesis of enantiopure cis- and trans-3-ethyl-4-piperidineacetates

Organic Letters

Volumn 4, Issue 16, 2002, Pages 2787-2790

  Amat, Mercedes ^a   Pérez, Maria ^a   Llor, Núria ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

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ARTICLE;

EID: 19044378567     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0263245     Document Type: Article

References (25)

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2. (b) Lounasmaa, M.; Tolvanen, A. In Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Series Ed.; John Wiley and Sons: Chichester, 1994; Vol. 25; Supplement to Part 4, Chapter 3.
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21. 2Bn) under a variety of conditions resulted in failure, the only identifiable product being the 2-pyridone formed by the opening of the oxazolidine ring promoted by the abstraction of an acidic C-8 proton.
22. Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 2599.
23. For a similar result, see: Mpango, G. B.; Mahalanabis, K. K.; Mahdavi-Damghani, Z.; Sniekus, V. Tetrahedron Lett. 1980, 21, 4823.
24. 2Et to trans-4 (32%) followed by desulfurization (93%).
25. Amat. M.; Cantó, M.; Llor, N.; Ponzo, V.; Pérez, M.; Bosch, J. Angew. Chem., Int. Ed. 2002, 41, 335.