An efficient preparation of α-alkyhdene-β-formylmethyl-γ-lactams via Pd(II)-catalyzed intramolecular alkyne-α,β-unsaturated carbonyl coupling

Synlett

Volumn , Issue 5, 2000, Pages 707-709

  Xie, Xu ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Coupling; Diastereoselectivity; Enynes; Lactams; Palladium

Indexed keywords

LACTAM;

ARTICLE; CATALYSIS; CYCLIZATION; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0034032558     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (12)

1. Trost, B. M. Pure Appl. Chem. 1994, 66, 2007.
2. Tsuji J. Palladium Reagents and Catalysts, Innovations in Organic Synthesis; John Wiley & Sons: Chichesler 1995.
3. Wang, Z.; Lu, X. Chem. Commun. 1996, 535, Wang, Z.; Lu, X. J. Org. Chem. 1996, 61, 2254.
4. Wang, Z.; Lu, X. Chem. Commun. 1996, 535, Wang, Z.; Lu, X. J. Org. Chem. 1996, 61, 2254.
5. Belaud, C.; Roussakis, C.; Latournoux, Y.; Alami, N. E.; Villierieras, J. Synth. Commun. 1985, 15, 1233. Kornet, M. J. J. Pharm. Sc. 1979, 68, 350. Ikuta, H.; Shirota, H.; Kobayashi, S.; Yamagishi, Y. Y.; Yamada, K.; Yamatsu, I.; Katayama, K. J. Med. Chem. 1987, 30, 1995.
6. Belaud, C.; Roussakis, C.; Latournoux, Y.; Alami, N. E.; Villierieras, J. Synth. Commun. 1985, 15, 1233. Kornet, M. J. J. Pharm. Sc. 1979, 68, 350. Ikuta, H.; Shirota, H.; Kobayashi, S.; Yamagishi, Y. Y.; Yamada, K.; Yamatsu, I.; Katayama, K. J. Med. Chem. 1987, 30, 1995.
7. Belaud, C.; Roussakis, C.; Latournoux, Y.; Alami, N. E.; Villierieras, J. Synth. Commun. 1985, 15, 1233. Kornet, M. J. J. Pharm. Sc. 1979, 68, 350. Ikuta, H.; Shirota, H.; Kobayashi, S.; Yamagishi, Y. Y.; Yamada, K.; Yamatsu, I.; Katayama, K. J. Med. Chem. 1987, 30, 1995.
8. 4) and concentrated, and the residue was subjected to column chromatography (eluent: petroleum ether/ethyl acetate) to give the cyclic product 2.
9. 9ON: 195.0684, Found: 195.0680.
10. The similar stereoisomers of β,γ-disubstituted γ-butyrolactones can be separated by column chromalography. See: a) Ma, S.; Lu, X. J. Org. Chem. 1991, 56, 5120.
11. b) Ma, S.; Zhu, G.; Lu, X. J. Org. Chem. 1993, 58, 3692.
12. 2NBr: 363.0834, Found: 363.0830.