Novel Wagner-Meerwein rearrangement of a bicyclo[3.1.1]heptanol under Mitsunobu conditions

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2235-2236

  Evans, P Andrew ^a   Nelson, Jade D ^a   Rheingold, Arnold L ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NORBORNANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0031592612     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00325-0     Document Type: Article

References (11)

1. 1. For a review on the rearrangement of pinane derivatives, see: Banthorpe, D. V.; Whittaker, D. Q. Rev., Chem. Soc. 1966, 20, 373.
2. 2. (a) Francisco, C. G.; Freire, R.; Hernández, R.; Melián, D.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1983, 24, 3907.
3. (b) Lemée, L.; Ratier, M.; Duboudin, J. -G.; Delmond, B, Synth. Commun. 1995, 25, 1313.
4. (c) Cruz Costa, M. C.; Johnstone, R. A. W.; Whittaker, D. J. Mol. Cat. A. 1996, 104, 251.
5. (d) Zhou, D.; Sheik, M.; Roth, H. D. Tetrahedron Lett. 1996, 37, 2385 and pertinent references cited therein.
6. 3. Cristol, S. J.; Aeling, E. O. J. Org. Chem. 1985, 50, 2698 and pertinent references cited therein.
7. 4. For recent reviews of the Mitsunobu reaction, see: (a) Mitsunobu, O. Synthesis 1981, 1.
8. (b) Hughes, D. L. Org. React. 1992, 42, 335.
9. 5. For examples of C-alkylation under Mitsunobu conditions, see: (a) Tsunoda, T.; Nagaku, M.; Nagino, C.; Kawamura, Y.; Ozaki, F.; Hioki, H.; Ito, S. Tetrahedron Lett. 1995, 36, 2531.
10. (b) Yu, J.; Cho, H. -S.; Falk, J. R. Tetrahedron Lett. 1995, 36, 8577 and pertinent references cited therein.
11. 2) = 10.88%.