Palladium catalysed rearrangement of allylic sulfoximines: Synthesis of γ-amino α,β-unsaturated ketones and esters

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5417-5420

  David, Dorothy M ^a   O'Meara, Gareth W ^a   Pyne, Stephen G ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ESTER DERIVATIVE; KETONE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030598005     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01060-X     Document Type: Article

References (17)

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3. 3. Maryanoff, B. E.; Greco, M. N.; Zhang, H.-G.; Andrade-Gordon, P.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A.; Brungs, P. H. J. Am. Chem. Soc. 1995, 117, 1225.
4. 4. Reetz, M. T.; Rohrig, D. Angew. Chem. Int. Ed. Engl. 1989, 28, 1706.
5. 5. For alternative syntheses from "the pool" of natural products see: (a) Monache, G. D., Giovanni, M. C. D.; Maggio, Misiti, D.; Zappia, G. Synthesis 1995, 1155.
6. (b) Mulzer, J.; Funk, G. Synthesis 1995, 101.
7. 6. Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H., J. Chem. Soc., Chem. Commun. 1995, 445.
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9. 8. Pyne, S. G.; Z. Dong, Z. J. Org. Chem. 1996, in press.
10. 9. Gais, H.-J.; Scommoda, M.; Lenz, D. Tetrahedron Lett. 1994, 35, 7361.
11. 10. This type of rearrangement would be the nitrogen analogue of the well described rearrangement of α-arylsulfinyl-β,γ-unsaturated compounds to γ-hydroxy α,β-unsaturated derivatives, see: (a) Kosugi, H.; Kitaoka, M.; Takahashi, A.; Uda, H. J. Chem. Soc. Chem. Commun. 1986, 1268.
12. (b) Tanikaga, R.; Nozaki, Y.; Tamura, T.; Kaji, A. Synthesis, 1983, 134.
13. (c) Burgess, K.; Cassidy, J.; Henderson, I. J. Org. Chem. 1991, 56, 2050 and references cited therein.
14. (d) de la Rosa, V. G.; Ordonez, M.; Alcudia, F.; Llera, J. M. Tetrahedron Lett. 1995, 36, 4889 and references cited therein.
15. (e) Dixon, D. E.; Kylie Hellmund K.; Pyne, S. G. J. Chem. Res. 1996, in press.
16. 11. Schaffner-Sabba, K.; Tomaselli, H.; Henrici, B.; Renfoe, H. B. J. Org. Chem. 1977, 42, 952.
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