Addition of allylstannanes to glycal epoxides. A diastereoselective approach to β-C-glycosidation

Tetrahedron Letters

Volumn 39, Issue 13, 1998, Pages 1709-1712

  Evans, David A ^a   Trotter, B Wesley ^a   Côté, Bernard ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; GLYCOSIDE;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; GLYCOSYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032568331     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00138-5     Document Type: Article

References (20)

1. 1) Recent reviews on C-glycosides: (a) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599;
2. (b) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon Press: Oxford, 1995.
3. 2) A few examples have been reported; β-C-glycosides from anomeric acetates: (a) Minehan, T. G.; Kishi, Y. Tetrahedron Lett. 1997, 39, 6815-6818; via episulfonium ions:
4. (b) Smolyakova, I. P.; Smit, W. A.; Zal'chenko, E. A.; Chizhov, O. S.; Shashkov, A. S. Tetrahedron Lett. 1993, 34, 3047-3050;
5. (c) Kawakami, H.; Ebata, T.; Koseki, K.; Okano, K.; Matsumoto, K.; Matsushita, H. Heterocycles 1993, 36, 2765-2776; via (putative) intermediate glycal epoxides:
6. (d) Shulman, M. L.; Shiyan, S. D.; Khorlin, A. Y. Carbohydrate Research 1974, 33, 229-235;
7. (e) Hanessian, S.; Liak, T. J.; Dixit, D. M. Carbohydrate Research 1981, 88, C14-C19.
8. 3) (a) Evans, D. A.; Trotter, B. W.; Côté, B.; Coleman, P. J.; Dias, L. C.; Tyler, A. N. Angewandte Chem. Int. Ed. Engl. 1997, 36, 2744-2748;
9. (b) Kobayashi, M.; Aoki, S.; Sakai, H.; Kihara, N.; Sasaki, T.; Kitagawa, I. Chem. Phar. Bull. 1993, 41, 989-991.
10. 4) Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661-6666.
11. 5) These experiments are precedented by a single example of β-selective cuprate addition to Brigl's anhydride: Bellosta, V.; Czernecki, S. J. Chem. Soc. Chem. Comm. 1989, 199-200. (equation presented)
12. 6) This result has recently been reported independently: Best, W. M.; Ferro, V.; Harle, J.; Stick, R. V.; Tilbrook, D. M., G. Aust. J. Chem. 1997, 50, 463-472.
13. 1H NMR coupling constants.
14. 8) Oppolzer, W.; Kundig, E. P.; Bishop, P. M.; Perret, C. Tetrahedron Lett. 1982, 23, 3901-3904; Oppolzer, W.; Schneider, P. Tetrahedron Lett. 1984, 25, 3305-3308.
15. 8) Oppolzer, W.; Kundig, E. P.; Bishop, P. M.; Perret, C. Tetrahedron Lett. 1982, 23, 3901-3904; Oppolzer, W.; Schneider, P. Tetrahedron Lett. 1984, 25, 3305-3308.
16. 9) Methallyl tributylstannane and epoxide 1 do not react in DMF at room temperature.
17. 10) Lewis, M. D.; Cha, K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978.
18. 11) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847-2853.
19. 12) We speculate that steric congestion around the reacting center lowers the nucleophilicity of the allylstannane. The consequent failure of the allylstannane addition to compete with nonproductive epoxide decomposition is presumed to be responsible for the lower yields observed for larger allylstannane protecting groups. Results in a similar system (epoxide 1) indicated that TBS (21% yield) and TBDPS (0% yield) protecting groups followed this trend.
20. 2Na: 597.3408; found: 597.3433 (FAB, m-nitrobenzyl alcohol, NaI added).