Synthesis of enantiopure ethyl (1S,9aS)- and (1S,9aR)-1-phenyl-4,9-dioxohexahydropyrrolo[1,2-d][1,4]oxazepine-9a(7H)-carboxylate by carbenoid/ylide/Stevens-[1,2]-shift with ring enlargement

Author:

Chelucci Giorgio,Saba Antonio,Valenti Raffaela,Bacchi Alessia

Publisher

Elsevier BV

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis

Reference11 articles.

1. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons: New York, 1997. West, F. G.; Naidu, B. N. J. Am. Chem. Soc. 1993, 115; 1177. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.

2. For a general review of the Stevens rearrangement, see Markò, I. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 913–73.

3. Ollis, W. D.; Rey, M.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1983, 1009.

4. Piperidines via Ammonium Ylide [1,2]-Shifts: A Concise, Enantioselective Route to (-)-Epilupinine from Proline Ester

5. Chelucci, G.; Saba, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 78. Chelucci, G.; Saba, A. Tetrahedron Lett. 1995, 36, 4673. Chelucci, G.; Saba, A.; Valle, G. Tetrahedron: Asymmetry 1995, 6, 807. Chelucci, G.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 699. Chelucci, G.; Culeddu, N.; Saba, A.; Valenti, R. Tetrahedron Lett. 1999, 40, 8269.

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