Catalytic asymmetric propionate aldol reactions via acyl halide-aldehyde cyclocondensations

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1883-1886

  Nelson, Scott G ^a   Wan, Zhonghui ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001339893     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005968e     Document Type: Article

References (29)

1. For an overview of a number of total syntheses incorporating asymmetric aldol bond constructions, see: (a) Mukaiyama, T. Tetrahedron 1999, 55, 8609-8670.
2. (b) Nicolaou, K. C.; Vourloumis, D.; Winssinger, N.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 44-122.
3. For recent asymmetric catalyzed additions of latent enolates, see: (a) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838.
4. (b) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039.
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7. (e) ref 1a. (f) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389.
8. For catalyzed asymmetric intermolecular aldol reactions, see: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396.
9. (b) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168-4178. For other examples of catalytic asymmetric aldol-type reactions, see:
10. Shibasaki, M.; Sasi, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256 and references therein.
11. Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406.
12. Nelson, S. G.; Peelen, T. J.; Wan, Z. J. Am. Chem. Soc. 1999, 121, 9742-9743.
13. Nelson, S. G.; Peelen, T. J.; Wan, Z. Tetrahedron Lett. 1999, 40, 6541-6543.
14. Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; VCH: Weinheim, 1970.
15. Pommier, A.; Pons, J.-M. Synthesis 1993, 441-459.
16. Acid bromides are superior to acid chlorides as ketene precursors in the catalyzed AAC reactions.
17. 4) and concentrated, and the crude product mixture was purified by flash chromatography (hexanes:ethyl acetate) or by bulb-to-bulb distillation.
18. 2O) and comparing the spectral and optical properties to those reported for the authentic material, see: Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171-7174. The stereochemistry of lactones 3b-h, 4, and 5 was assigned by analogy to this determination and to the stereochemical outcome of the analogous acetyl bromide AAC reactions. See ref 4.
19. For recent examples of asymmetric catalytic syntheses of optically active propargylic alcohols, see: (a) Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738-8739.
20. (b) Tao, B.; Ruble, J. C.; Diego A. Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091-5092.
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22. Moyano, A.; Pericas, M. A.; Valenti, E. J. Org. Chem. 1989, 54, 573-582.
23. Cyclocondensations employing aromatic aldehydes previously afforded cinnamic acid derivatives in good yield: Nelson, S. G.; Wan, Z. Unpublished results.
24. For previous asymmetric cycloadditions utilizing trimethylsilylketene, see: (a) Romo, D.; Harrison, P. H. M.; Jenkins, S. I.; Riddoch, R. W.; Park, K.; Yang, H. W.; Zhao, C.; Wright, G. D. Bioorg. Med. Chem. 1998, 6, 1255-1272 and references therein.
25. (b) Yang, H. W.; Romo, D. Tetrahedron Lett. 1998, 39, 2877-2880.
26. Dymock, B. W.; Kocienski, P. J.; Pons, J.-M. Synthesis 1998, 1655-1661.
27. The low-temperature ring opening of alkynyl lactones using stoichiometric quantities of the metal alkoxide affords superior yields relative to the previously reported lanthanum(tert-butoxide)-catalyzed lactone alcoholysis, see: Nelson, S. G.; Wan, Z.; Peelen, T. J.; Spencer, K. L. Tetrahedron Lett. 1999, 40, 6535-6539.
28. For the conversion of morpholine amides to ketones, see: Martín, R.; Romea, P.; Tey, C.; Urpí, F.; Vilarrasa, J. Synlett 1997, 1414-1416.
29. Garigipati, S. G.; Tschaen, D. M.; Weinreb, S. M. J. Am. Chem. Soc. 1985, 107, 7790.