8-endo versus 5-exo cyclization of unsaturated acrylate esters upon reaction with t-BuHgI/KI

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2557-2560

  Russell, Glen A ^a   Li, Chaozhong ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; OXEPINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029928210     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00329-2     Document Type: Article

References (11)

1. Russell, G.A. Acc.Chem.Res. 1989, 22, 1-8.
2. 2R in almost quantitative yield.
3. Russell, G.A.; Li, C.; Chen, P. J.Am.Chem.Soc. 1995, 117, 3645-3646.
4. Lee, E.; Yoon, C.H.; Lee, T.H. J.Am.Chem.Soc. 1992, 114, 10981-10983.
5. Pirrung, F.O.H.; Hiemstra, H.; Speckamp, W.N.; Kaptein, B.; Schoemaker, H.E. Synthesis 1995, 458-472.
6. Belletire, J.L.; Mahmoodi, N.O. Tetrahedron Lett. 1989, 30, 4363-4366.
7. Clough J.M.; Pattenden, G.; Wight, P.G. Tetrahedron Lett. 1989, 30, 7469-7472.
8. Hanessian, S.; Di Fabio, R.; Marcoux, J.-F.; Prud'homme, M. J.Org.Chem. 1990, 55, 3436-3438.
9. 2S: 306.1654. Found: 306.1661.
10. NOE is observed in 3b,g,h between the α-methine hydrogens and both other methine hydrogens. This NOE is not observed in the trans isomers of 3c or 3e. 11. The organomercurial 4i or 4j could be trapped by PhSeSePh (2 eq.) to give the corresponding monocyclized selenide compounds, whose stereochemistry was demonstrated by their NOESY spectra.
11. 13C NMR and HRMS.