Influence of the solvent polarity on the stereoselectivity of the uncatalyzed [4+2] cycloaddition of cyclopentadiene to N,N'-fumaroyldi[(2r)- borane-10,2-sultam]

Helvetica Chimica Acta

Volumn 81, Issue 12, 1998, Pages 2314-2325

  Chapuis, Christian ^a,c   Kucharska, Anna ^b   Rzepecki, Piotr ^b   Jurczak, Janusz ^a,b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b UNIVERSITY OF WARSAW   (Poland)

^c Analysis and Perception Department   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; BETA CYCLODEXTRIN; BORNANE DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; N,N' FUMAROYLDI(BORNANE 10,2 SULTAM); SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032414490     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1522-2675(19981216)81:12<2314::AID-HLCA2314>3.0.CO;2-I     Document Type: Article

References (13)

1. C. Chapu, P. Rzepecki, T. Bauer, J. Jurczak, Helv. Chim. Acta 1995, 78, 145.
2. T. Bauer, C. Chapuis, A. Kucharska, P. Rzepecki, J. Jurczak, Helv. Chim. Acta 1998, 81, 324.
3. C. Chapuis, J. Y. de Saint-Laumer, M. Marty, Helv. Chim. Acta 1997, 80, 146;
4. G. Bernardinelli, C. Chapuis, A. J. Kingma, M. Wills, Helv. Chim. Acta, ibid. 1997, 80, 1607.
5. M. E. Burrage, R. C. Cookson, S. S. Gupte, I. D. R. Stevens, J. Chem. Soc., Perkin Trans. 2 1975, 1325;
6. A. I. Konovalov, J. P. Breus, I. A. Sharagin, V. D. Kiselev, J. Org. Chem. USSR 1979, 15, 315;
7. M. Ahmad, J. Hamer, J. Org. Chem. 1966, 31, 2831;
8. P. Haberfield, A. K. Ray, J. Org. Chem., ibid. 1972, 37, 3093.
9. a) D. J. Jaeger, C. E. Tucker, Tetrahedron Lett. 1989, 30, 1785;
10. B) R. Breslow, T. Guo, J. Am. Chem. Soc. 1988, 110, 5613;
11. c) R. Braun, J. Sauer, Chem. Ber. 1986, 119, 1269;
12. d) R. Breslow, U. Maitra, D. Rideout, Tetrahedron Lett. 1983, 24, 1901;
13. e) J. A. Berson, Z. Hamlet, W. A. Mueller, J. Am. Chem. Soc. 1962, 84, 297.