Diastereoselective manipulations of bicyclo[m.1.0] alkane derivatives. 3. Nucleophilic additions to the carbonyl carbon of (1R,8R)-Bicyclo[6.1.0]nonan-2,6-dione 2-(2S,3S)-1,4-Di-O-methyl-1,2,3,4-butane ketal

Tetrahedron

Volumn 53, Issue 27, 1997, Pages 9043-9056

  Mash, Eugene A ^a   Nimkar, Kalpana S ^a   Baron, James A ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; KETONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; DIASTEREOISOMER; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0030996357     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00615-7     Document Type: Article

References (21)

1. Mash, E. A.; Gregg, T. M.; Stahl, M. T.; Walters, W. P. J. Org. Chem. 1996, 61, 2738-2742.
2. Part 2: Mash, E. A.; Gregg, T. M.; Kaczynski, M. A. J. Org. Chem. 1996, 61, 2743-2752.
3. Enantiomerically enriched bicyclo[m.1.0]alkan-2-ones 1 are readily prepared from 2-cycloalken-1-one ketals; see (a) Mash, E. A.; Nelson, K. A. Tetrahedron 1987, 43, 679-692.
4. (b) Mash, E. A.; Torok, D. S. J. Org. Chem. 1989, 54, 250-253. Mash, E. A.; Math, S. K.; Arterburn, J. A. J. Org. Chem. 1989, 54, 4951-4953.
5. (b) Mash, E. A.; Torok, D. S. J. Org. Chem. 1989, 54, 250-253. Mash, E. A.; Math, S. K.; Arterburn, J. A. J. Org. Chem. 1989, 54, 4951-4953.
6. (c) Yeh, S.-M.; Huang, L.-H.; Luh, T.-Y. J. Org. Chem. 1996, 61, 3906-3908.
7. (a) Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981-3996.
8. (b) Still, W. C. In Current Trends in Organic Synthesis; Pergamon Press: Tokyo, Japan, 1982; pp 233-246.
9. (a) BATCHMIN, 4.0; Columbia University: New York, 1993.
10. (b) Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comp. Chem. 1990, 11, 440-467.
11. Conformers with carbonyls disposed so that the Re face is clearly more exposed to attack include 1-11 (0.6%), 1-18 (0.3%), 1-19 (0.3%), 1-29 (0.1%), 1-36 (0.1%), 1-43 (0.1%), and 1-45 (0.1%). Conformer 1-40 (0.1%) is the lowest energy conformer in which the Si face is clearly more exposed to attack.
12. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994, pp 731-737 and references cited in therein.
13. The conformational ensemble for cyclohexanone was obtained using a Monte Carlo search strategy and the MM2* force field resident in BATCHMIN v4.0.
14. (a) Bürgi, H. B.; Dunitz, J. D.; Lehn, J. M.; Wipff, G. Tetrahedron 1974, 30, 1563-1572.
15. (b) Bürgi, H.-B. Angew. Chem., Int. Ed. Engl. 1975, 14, 460-473.
16. Ashby, E. C.; Laemmle, J. T. Chem. Rev. 1975, 75, 521-546.
17. 5-(Benzyloxy)cyclooctanone (2) can be prepared in large quantities in two steps from cis-1,5-cyclooctanediol; see McMurry, J. E.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 10167-10173.
18. Schmidt, M.; Amstutz, R.; Crass, G.; Seebach, D. Chem. Ber. 1980, 113, 1691-1707.
19. Marquet, A.; Jacques, J. Bull. Soc. Chim. Fr. 1962, 90-96.
20. Hiemstra, H.; Wynberg, H. Tetrahedron Lett. 1977, 18, 2183-2186.
21. Preparation of zinc-copper couple: Shank, R. S.; Shechter, H. J. Org. Chem. 1959, 24, 1825-1826.