Highly stereoselective addition of 2-trimethylsilyloxyfuran to N-glyoxyloyl-(2R)-bornane-10,2-sultam

Tetrahedron Asymmetry

Volumn 7, Issue 4, 1996, Pages 981-984

  Bauer, Tomasz ^a  

^a UNIVERSITY OF WARSAW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

BORNANE DERIVATIVE; FURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0029965918     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00097-3     Document Type: Article

References (15)

1. T. Bauer, A. Jezewski, C. Chapuis, J. Jurczak, Tetrahedron: Asymmetry, accepted for publication.
2. W. Oppolzer, C. Chapuis, G. Bernardinelli, Helv. Chim. Acta, 1984, 67, 1397
3. T. Bauer, C. Chapuis, J. Kozak, J. Jurczak, Helv. Chim. Acta, 1989, 72, 482-6.
4. T. Bauer, C. Chapuis, A. Jezewski, J. Kozak, J. Jurczak, Tetrahedron: Asymmetry, accepted for publication.
5. J. Jurczak, A. Jezewski, Tetrahedron: Asymmetry, accepted for publication.
6. T. Bauer, J. Kozak, C. Chapuis, J. Jurczak, J. Chem. Soc. Chem. Commun., 1990, 1178-9.
7. T. Bauer, A. Jezewski, J. Jurczak, Tetrahedron: Asymmetry, accepted for publication.
8. G. Casiraghi, L. Colombo, G. Rassu, P. Spanu, G. Gasparri Fava, M. Ferrari Belicchi, Tetrahedron, 1990, 46, 5807-5824.
9. G. Rassu, P. Spanu, G. Casiraghi, L. Pinna, Tetrahedron, 1991, 47, 8025-8030.
10. J. Jurczak, A. Golebiowski, T. Bauer, Synthesis, 1985, 928-9.
11. G. Casiraghi, L. Colombo, G. Rassu, P. Spanu, J. Org. Chem. 1990, 55, 2565-67.
12. 3 were added, followed by slow addition of 0.5 mL (3.04 mmol) of TMSOF 2. The solution was stirred at room temperature overnight, then solvent were evaporated using a rotary evaporator. The residue was subjected to flash chromatography (hexane - ethyl acetate as eluent) yielding 20 mg of 6, 23 mg of 4 and 646 mg of 3. Overall yield - 92%, de 88%.
13. 45=3.3). 3.95 (1H, t), 3.53 (2H, q), 1.3-2.2(7H, m), 1.15 (3H, s), 0.98 (3H, s), 0.11 (9H, s).
14. -1. The final R was 0.0490 (unit weights).
15. T. Bauer, J. W. Krajewski, manuscript in preparation.