Six-membered annulation reaction by sequential η3-allylpalladium alkylation-Michael addition

Tetrahedron Letters

Volumn 39, Issue 11, 1998, Pages 1349-1352

  Jousse, Céline ^a   Mainguy, Delphine ^a   Desmaële, Didier ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ERYTHRINA ALKALOID; ESTER; NITRO DERIVATIVE; PALLADIUM;

ALKYLATION; ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 0032510356     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10833-4     Document Type: Article

References (22)

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3. 2Me, n = 0) in 82 % yield.
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12. 11. Formation of ketone 12 before any acidic workup precluded a Nef type mechanism.
13. 12. Nakashita, Y.; Hesse, M. Helv. Chim. Acta 1983, 66, 845-860.
14. 6N: C, 59.80; H, 5.96; N, 4.35. Found: C, 59.62; H, 5.99; N, 4.26.
15. 3, 200 MHz) δ 6.99 (s, 1H), 6.98 (d, J = 9.5 Hz, 1H), 6.78 (d. J = 9.5 Hz, 1H), 5.97 (s, 2H), 3.61 (s, 3H), 2.97 (m, 1H), 2.35 (d, J = 12 Hz, 1H), 2.25 (d, J = 12 Hz, 1H), 2.00-1.80 (m, 2H), 1.60-1.20 (m, 6H).
16. 15. Aleksandrowicz, P.; Piotrowska, H.; Sas, W. Tetrahedron 1982, 38, 1321-1327. Wade, P. A.; Morrow, S. D.; Hardinger, S. A. J. Org. Chem. 1982, 47, 365-367.
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19. 16 gave an inseparable mixture of 1,2 and 1,4 reduction alcohols.
20. 4: C, 69.83; H, 8.27. Found: C, 69.68; H, 8.30.
21. 19. Bedekar, A. V.; Watanabe, T.; Tanaka, K.; Fuji, K. Synthesis 1995, 1069-1070.
22. 2).