Sequential nitromethane conjugate addition/elimination - Pd-catalyzed allylation of β-trifloxy acrylates. Application to carbapenem synthesis

Organic Letters

Volumn 1, Issue 11, 1999, Pages 1783-1785

  Chung, John Y L ^a   Grabowski, Edward J J ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001406203     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990299u     Document Type: Article

References (14)

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5. Yasuda, N.; Yang, C.; Wells, K. M.; Jensen, M. S.; Hughes, D. Tetrahedron. Lett. 1999, 40, 427 and references therein.
6. Boyd, G. V. In Supplement F2: The chemistry of amino, nitroso, and related groups; Patai, S., Ed.; Wiley: New York, 1996.
7. Tamura, R.; Kamimura, A.; Ono, N. Synthesis 1991, 423.
8. Yoshioka, T.; Yamamoto, K.; Shimauchi, Y.; Fukagawa, Y.; Ishikura, T. J. Chem. Soc., Chem. Commun. 1984, 1513.
9. Yasuda, N.; Huffman, M. A.; Ho, G.-J.; Xavier, L. C.; Yang, C.; Emerson, K. M.; Tsay, F.-R.; Li, Y.; Kress, M. H.; Rieger, D. L.; Karady, S.; Sohar, P.; Abramson, N. L.; DeCamp, A. E.; Mathre, D. J.; Douglas, A. W.; Dolling, U.-H.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1998, 63, 5438.
10. +).
11. Previous studies indicated that HMPA or DMPU can stabilize the carbapenem: see ref 5.
12. Based on LC area % at 260 nm.
13. Available from Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA 92612.
14. Humphrey, G. R.; Miller, R. A.; Lieberman, D. R. W.O. Patent 9851677, 1998.