Palladium-catalysed [3 + 2]-cycloaddition reactions employing sulphonyl-activated unsaturated carbohydrate derivatives

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2303-2306

  Holzapfel, Cedric W ^a   Van Der Merwe, Thilo L ^a  

^a UNIVERSITY OF JOHANNESBURG   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

AJMALICINE; ALKALOID; TETRAHYDROALSTONINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029947404     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00249-3     Document Type: Article

References (14)

1. For some review articles see: Oppolzer, W. Angew. Chem. Int. Ed. Engl. 1977, 16, 10; Kozikowski, A.P. Ace. Chem. Res. 1984, 17, 410.
2. For some review articles see: Oppolzer, W. Angew. Chem. Int. Ed. Engl. 1977, 16, 10; Kozikowski, A.P. Ace. Chem. Res. 1984, 17, 410.
3. Trost, B.M. Angew. Chem. Int. Ed. Engl. 1986, 25, 1; Trost, B.M. Pure Appl. Chem. 1988, 60, 1615.
4. Trost, B.M. Angew. Chem. Int. Ed. Engl. 1986, 25, 1; Trost, B.M. Pure Appl. Chem. 1988, 60, 1615.
5. Shimizu, I.; Ohashi, Y.; Tsuji, J. Tetrahedron Lett. 1984, 25, 5183; Trost, B.M.; Chan, D.M.T.; Nanninga, T.N. Org. Synth. 1984, 62, 58.
6. Shimizu, I.; Ohashi, Y.; Tsuji, J. Tetrahedron Lett. 1984, 25, 5183; Trost, B.M.; Chan, D.M.T.; Nanninga, T.N. Org. Synth. 1984, 62, 58.
7. Trost, B.M.; Chan, D.M.T. J. Am. Chem. Soc. 1983, 105, 2315.
8. Van der Merwe, T.L. Ph. D. thesis, Rand Afrikaans University 1994.
9. 2 (3 mg, 0.013 mmol) with tri-isopropylphosphite (20 μl, 0.077 mmol), followed by stirring at ambient temperature for 30 min.
10. 6 was added sulphone 20 [150 mg, 0.487 mmol in toluene (2 ml)] and 2-[(trimethylsilyl)methyl]-2-propen-1-yl acetate (124 μl, 1.2 eq.). The reaction mixture was placed in a preheated (150°C) oil bath, and was heated under reflux for two hours. The solvent was removed in vacuo, and the residue was subjected to flash chromatography (EtOAc/hexane: 1/3) to afford bicycle 21.
11. 2O, 37%).
12. Trost, B.M.; Miller, M.L. J. Am. Chem. Soc. 1988, 110, 3687.
13. Trost, B.M.; Arndt, H.C.; Strege, P.E.; Verhoeven, T.R. Tetrahedron Lett. 1976, 3477.
14. Trost, B.M.; Sleoane, P.; Mignanin, S.; Acemoglu, M. J. Am. Chem. Soc. 1989, 111, 7487.