Diastereoselective Synthesis of Metal Carbene-Functionalized Spirocyclic Carbohydrates

Synlett

Volumn 1996, Issue 10, 1996, Pages 995-996

  Dötz, Karl Heinz ^a   Neuß, Oliver ^a   Nieger, Martin ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038858123     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5641     Document Type: Article

References (30)

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2. Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617.
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4. Robinson, J. A. Fortschr. Chem. Org. Naturst. 1991, 58, 1.
5. For metal-induced cycloisomerization of alkynols, see: Bruce, M. I.; Swincer, A. G.; Thomson, B. J.; Wallis, R. C. Aust. J. Chem. 1980, 33, 2605; Dötz, K. H.; Sturm, W.; Alt, H. G. Organometallics 1987, 6, 1424; Parlier, A.; Rudler, H. ibid. 1986, 5, 514; McDonald, F. E.; Gleason, M. M. Angew. Chem. Int. Ed. Engl. 1995, 44, 350; Schmidt, B.; Kocienski, P.; Reid, G. Tetrahedron 1996, 52, 1617; Quayle, P.; Ward, E. L. M.; Taylor, P. Tetrahedron Lett. 1994, 35, 8883.
6. For metal-induced cycloisomerization of alkynols, see: Bruce, M. I.; Swincer, A. G.; Thomson, B. J.; Wallis, R. C. Aust. J. Chem. 1980, 33, 2605; Dötz, K. H.; Sturm, W.; Alt, H. G. Organometallics 1987, 6, 1424; Parlier, A.; Rudler, H. ibid. 1986, 5, 514; McDonald, F. E.; Gleason, M. M. Angew. Chem. Int. Ed. Engl. 1995, 44, 350; Schmidt, B.; Kocienski, P.; Reid, G. Tetrahedron 1996, 52, 1617; Quayle, P.; Ward, E. L. M.; Taylor, P. Tetrahedron Lett. 1994, 35, 8883.
7. For metal-induced cycloisomerization of alkynols, see: Bruce, M. I.; Swincer, A. G.; Thomson, B. J.; Wallis, R. C. Aust. J. Chem. 1980, 33, 2605; Dötz, K. H.; Sturm, W.; Alt, H. G. Organometallics 1987, 6, 1424; Parlier, A.; Rudler, H. ibid. 1986, 5, 514; McDonald, F. E.; Gleason, M. M. Angew. Chem. Int. Ed. Engl. 1995, 44, 350; Schmidt, B.; Kocienski, P.; Reid, G. Tetrahedron 1996, 52, 1617; Quayle, P.; Ward, E. L. M.; Taylor, P. Tetrahedron Lett. 1994, 35, 8883.
8. For metal-induced cycloisomerization of alkynols, see: Bruce, M. I.; Swincer, A. G.; Thomson, B. J.; Wallis, R. C. Aust. J. Chem. 1980, 33, 2605; Dötz, K. H.; Sturm, W.; Alt, H. G. Organometallics 1987, 6, 1424; Parlier, A.; Rudler, H. ibid. 1986, 5, 514; McDonald, F. E.; Gleason, M. M. Angew. Chem. Int. Ed. Engl. 1995, 44, 350; Schmidt, B.; Kocienski, P.; Reid, G. Tetrahedron 1996, 52, 1617; Quayle, P.; Ward, E. L. M.; Taylor, P. Tetrahedron Lett. 1994, 35, 8883.
9. For metal-induced cycloisomerization of alkynols, see: Bruce, M. I.; Swincer, A. G.; Thomson, B. J.; Wallis, R. C. Aust. J. Chem. 1980, 33, 2605; Dötz, K. H.; Sturm, W.; Alt, H. G. Organometallics 1987, 6, 1424; Parlier, A.; Rudler, H. ibid. 1986, 5, 514; McDonald, F. E.; Gleason, M. M. Angew. Chem. Int. Ed. Engl. 1995, 44, 350; Schmidt, B.; Kocienski, P.; Reid, G. Tetrahedron 1996, 52, 1617; Quayle, P.; Ward, E. L. M.; Taylor, P. Tetrahedron Lett. 1994, 35, 8883.
10. For metal-induced cycloisomerization of alkynols, see: Bruce, M. I.; Swincer, A. G.; Thomson, B. J.; Wallis, R. C. Aust. J. Chem. 1980, 33, 2605; Dötz, K. H.; Sturm, W.; Alt, H. G. Organometallics 1987, 6, 1424; Parlier, A.; Rudler, H. ibid. 1986, 5, 514; McDonald, F. E.; Gleason, M. M. Angew. Chem. Int. Ed. Engl. 1995, 44, 350; Schmidt, B.; Kocienski, P.; Reid, G. Tetrahedron 1996, 52, 1617; Quayle, P.; Ward, E. L. M.; Taylor, P. Tetrahedron Lett. 1994, 35, 8883.
11. Reviews: Dötz, K. H. Angew. Chem. Int. Ed. Engl. 1984, 23, 587; Wulff, W. D. In Comprehensive Organometallic Chemistry II, Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995, Vol. 12, p 469; Hegedus, L. S. ibid., Vol. 12, p 549; Harvey, D F.; Sigano, D. M. Chem. Rev. 1996, 96, 271; de Meijere, A. Pure Appl. Chem. 1996, 68, 61.
12. Reviews: Dötz, K. H. Angew. Chem. Int. Ed. Engl. 1984, 23, 587; Wulff, W. D. In Comprehensive Organometallic Chemistry II, Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995, Vol. 12, p 469; Hegedus, L. S. ibid., Vol. 12, p 549; Harvey, D F.; Sigano, D. M. Chem. Rev. 1996, 96, 271; de Meijere, A. Pure Appl. Chem. 1996, 68, 61.
13. Reviews: Dötz, K. H. Angew. Chem. Int. Ed. Engl. 1984, 23, 587; Wulff, W. D. In Comprehensive Organometallic Chemistry II, Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995, Vol. 12, p 469; Hegedus, L. S. ibid., Vol. 12, p 549; Harvey, D F.; Sigano, D. M. Chem. Rev. 1996, 96, 271; de Meijere, A. Pure Appl. Chem. 1996, 68, 61.
14. Reviews: Dötz, K. H. Angew. Chem. Int. Ed. Engl. 1984, 23, 587; Wulff, W. D. In Comprehensive Organometallic Chemistry II, Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995, Vol. 12, p 469; Hegedus, L. S. ibid., Vol. 12, p 549; Harvey, D F.; Sigano, D. M. Chem. Rev. 1996, 96, 271; de Meijere, A. Pure Appl. Chem. 1996, 68, 61.
15. Reviews: Dötz, K. H. Angew. Chem. Int. Ed. Engl. 1984, 23, 587; Wulff, W. D. In Comprehensive Organometallic Chemistry II, Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995, Vol. 12, p 469; Hegedus, L. S. ibid., Vol. 12, p 549; Harvey, D F.; Sigano, D. M. Chem. Rev. 1996, 96, 271; de Meijere, A. Pure Appl. Chem. 1996, 68, 61.
16. Yamamoto, H. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds.; Pergamon; Oxford 1991, Vol. 2, p 81.
17. Brandsma, L.; Verkruijsse, H. Preparative Polar Organometallic Chemistry 1, Springer, Berlin, 1987, p 63.
18. For a general protocol of the oxidation of carbohydrates, see: Hanessian, S.; Ugolini, A. Carbohydr. Res. 1984, 130, 261.
19. General procedure for the synthesis of carbohydrate butynols: In an argon atmosphere allenyl magnesium bromide (5.4 mmol), dissolved in 27 ml diethyl ether, was added to a solution of the carbonyl compound (2.7 mmol) in 10 ml anhydrous THF at - 78°C. The mixture was stirred for Ih at -78°C and finally 10 min without cooling. After the addition of aqueous ammonium chloride (10 ml) the organic layer was separated and the aqueous layer was extracted three times with THF. The combined organic extracts were dried over magnesium sulfate and concentrated to dryness. The oily residue can be purified by flash chromatography (8) or recrystallization (5, 2).
20. 2) = 0.078 (R(F) = 0.031 for I > 2σ(I)). Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre.
21. Reetz, M. T. Angew. Chem. Int. Ed. Engl. 1984, 23, 556.
22. 5THF (3.35 mmol) in 70 ml anhydrous THF. The solution was concentrated to half the volume and stirred at the temperature and for the period of time as indicated in the table. The solvent was evaporated in vacuo and the crude product was purified by flash chromatography.
23. 3, 20°C): δ 346.6, 222.7, 216.2, 138.6, 129.1, 128.8, 126.8, 112.7, 110.0, 105.4, 103.6, 75.3, 73.0, 72.2, 71.1, 61.4, 38.9, 31.6, 26.7, 26.4, 25.3, 25.1.
24. Kreiter, C. G. Angew. Chem. Int. Ed. Engl. 1968, 7, 390, Casey, C P.; Brunsvold, W. R. J. Organomet. Chem. 1976, 118, 309.
25. Kreiter, C. G. Angew. Chem. Int. Ed. Engl. 1968, 7, 390, Casey, C P.; Brunsvold, W. R. J. Organomet. Chem. 1976, 118, 309.
26. Lattuada, L.; Licandro, E.; Maiorana, S.; Papagni, A. Gazz. Chim. It. 1993, 123, 31
27. Dötz, K H. Angew. Chem. Int. Ed. Engl. 1975, 14, 644.
28. Wulff, W. D.; Bauta, W. E.; Kaesler, R. W.; Lankford, P. J., Miller, R. S.; Murray, C. K.; Yang, D. C. J. Am. Chem. Soc. 1990, 12, 3642.
29. Sheldrick, G. M. SHELXTL-PLUS, Siemens Analytical X-ray Instruments Inc., Madison, WI, 1989.
30. Sheldrick, G. M. SHELXTL-93, Universität Göttingen, 1993.