Nitro-activated double bonds in Pd(0)-catalysed [3 + 2]-cycloaddition reactions

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2307-2310

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

^a UNIVERSITY OF JOHANNESBURG   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; INDAN DERIVATIVE; PYRAN DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029989537     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00250-X     Document Type: Article

References (9)

1. a) Trost, B.M.; Chan, D.M.T. J. Am. Chem. Soc. 1981, 103, 5972;
2. b) Shimizu, I.; Ohashi, Y.; Tsuji, J. Tetrahedron Lett. 1984, 25, 5183;
3. c) Holzapfel, C.W.; van der Merwe, T.L. Tetrahedron Lett. this issue.
4. a) Marais, C.F. M.Sc. dissertation, Rand Afrikaans University 1981;
5. b) Herbst, M. M.Sc. dissertation, Rand Afrikaans University 1993.
6. 2 (3 mg, 0.013 mmol) with tri-isopropylphosphite (20 μl, 0.077 mmol), followed by stirring at ambient temperature for 30 min.
7. 3 were added methyl ether 7 [80 mg, 0.343 mmol in THF (2 ml)] and 2-[(trimethylsilyl)methyl]-2-propen-1-yl acetate (88 μl, 0.446 mmol). The reaction mixture was placed in a preheated (90°C) oil bath, and was heated under reflux for five hours. The solvent was removed in vacuo, and the residue was subjected to flash chromatography (EtOAc/hexane: 1/4) to afford bicycles 8 and 9.
8. 4O, 23%).
9. Van der Merwe, T.L. Ph. D. thesis, Rand Afrikaans University 1994.