Diastereoselective Michael Reactions of Azomethine Ylides to Chiral 4-Methyleneoxazolidin-5-ones: Synthesis of the Four Stereoisomers of 4-Benzamidopyroglutamate

Synlett

Volumn 1997, Issue 1, 1997, Pages 100-102

  Javidan, Abdollah ^a   Schafer, Karl ^a   Pyne, Stephen G ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

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[No Author keywords available]

Indexed keywords

EID: 0002782416     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (13)

1. Tatsukawa, A.; Kawatake, K.; Kanemasa, S.; Rudzinski, J. M. J. Chem. Soc. Perkin Trans. 2 1994, 2525 and references cited therein.
2. For some recent references see: (a) Grigg, R. Tetrahedron : Asymmetry 1995, 6, 2475 and references cited therein. (b) Galley, G.; Liebscher, J.; Patzel, M. J. Org. Chem. 1995, 60, 5005. (c) Anslow, A. S.; Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 2465. (d) Waldmann, H.; Blaser, E.; Jansen, M.; Letschert, H.-P. Angew. Chem. Int. Ed. Engl. 1994, 33, 683.
3. For some recent references see: (a) Grigg, R. Tetrahedron : Asymmetry 1995, 6, 2475 and references cited therein. (b) Galley, G.; Liebscher, J.; Patzel, M. J. Org. Chem. 1995, 60, 5005. (c) Anslow, A. S.; Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 2465. (d) Waldmann, H.; Blaser, E.; Jansen, M.; Letschert, H.-P. Angew. Chem. Int. Ed. Engl. 1994, 33, 683.
4. For some recent references see: (a) Grigg, R. Tetrahedron : Asymmetry 1995, 6, 2475 and references cited therein. (b) Galley, G.; Liebscher, J.; Patzel, M. J. Org. Chem. 1995, 60, 5005. (c) Anslow, A. S.; Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 2465. (d) Waldmann, H.; Blaser, E.; Jansen, M.; Letschert, H.-P. Angew. Chem. Int. Ed. Engl. 1994, 33, 683.
5. For some recent references see: (a) Grigg, R. Tetrahedron : Asymmetry 1995, 6, 2475 and references cited therein. (b) Galley, G.; Liebscher, J.; Patzel, M. J. Org. Chem. 1995, 60, 5005. (c) Anslow, A. S.; Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 2465. (d) Waldmann, H.; Blaser, E.; Jansen, M.; Letschert, H.-P. Angew. Chem. Int. Ed. Engl. 1994, 33, 683.
6. Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875.
7. Tatsukawa, A.; Dan, M. D.; Ohbatake, M.; Kawatake, K.; Fukata, T.; Wada, E.; Kanemasa, S.; Kakei, S. J. Org. Chem. 1993, 58, 4221.
8. Pyne, S. G.; Safaei-G, J. Tetrahedron Lett. 1995, 36, 2511.
9. Kanemasa, S.; Uchida, O.; Wada, E. J. Org. Chem. 1990, 55, 4411.
10. t) and 16: δ 1.48 (s, 9H), 2.45 ( ddd, J = 13, 9, 6 Hz, 1H, H3a), 2.85 (ddd, J = 13, 9, 2 Hz, 1H, H3b), 4.20 (ddd, J = 9, 2, 1.5 Hz, 1H, H2), 4.60 (ddd, J = 9, 6, 6 Hz, 1H, H4), 6.81 (br. s, 1H, NH), 7.21 (br. s, 1H, NH), 7.35 - 7.80 (m, 5H, ArH). 14 and 20: δ 1.47 (s, 9H), 2.05 ( ddd, J = 12.6, 9.6, 6.5 Hz, 1H, H3a), 3.12 (ddd, J = 12.6, 8, 6.3 Hz, 1H, H3b), 4.22 (dd, J = 9, 7.2 Hz, 1H, H2), 4.89 (dd, J = 16.8, 9 Hz, 1H, H4), 7.20 - 7.80 (m, 7H, ArH and 2 x NH).
11. To be published in a full paper. The absolute stereochemistry of the minor diastereoisomers of 4 and 5 was not determined since these compounds were never isolated injure form.
12. McIntosh, J. M.; Leavitt, R. K.; Mishra, P.; Cassidy, K. C.; Drake, J. E.; Chadha, R. J. Org. Chem. 1988, 53, 1947.
13. Pyne, S. G.; Javidan, A.; Skelton, B. W.; White, A. H. Tetrahedron 1995, 51, 5157.