Stereoselective 1,2-additions of α-alkoxymethyllithiums to aldehydes

Organic Letters

Volumn 3, Issue 18, 2001, Pages 2903-2906

  Smyj, Robert P ^a   Chong, J Michael ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

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EID: 0013263863     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016384v     Document Type: Article

References (38)

1. Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757-824.
2. Asymmetric γ-alkoxyallyl additions: (a) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535-1538.
3. (b) Yamamoto, Y.; Kobayashi, K.; Okano, H.; Kadota, I. J. Org. Chem. 1992, 57, 7003-7005.
4. (c) Roush, W. R.; VanNieuwenhze, M. S. J. Am. Chem. Soc. 1994, 116, 8536-8543.
5. (d) Coleman, R. S.; Kong, J.-S.; Richardson, T. E. J. Am. Chem. Soc. 1999, 121, 9088-9095. Heteroatom functionalized chiral organozines:
6. (e) Eisenberg, C.; Knochel, P. J. Org. Chem. 1994, 59, 3760-3761.
7. (f) Ostwlad, R.; Chavant, P.-Y.; Stadmüller, H.; Knochel, P. J. Org. Chem. 1994, 59, 4143-4153.
8. (g) Lütjens, H.; Nowotny, S.; Knochel, P. Tetrahedron: Asymmetry 1995, 6, 2675-2678. Related organotitaniums:
9. (h) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473-7484.
10. (a) McGarvey, G. J.; Kimura, M. J. Org. Chem. 1982, 47, 5422-5424.
11. (b) McDougal, P. G.; Condon, B. D.; Laffose, M. D., Jr.; Lauro, A. M.; VanDerveer, D. Tetrahedron Lett. 1988, 29, 2547-2550.
12. (c) Yamada, J.-I.; Abe, H.; Yamamoto, Y. J. Am. Chem. Soc. 1990, 112, 6118-6120.
13. (d) Tsunoda, T.; Fujiwara, K.; Yamamoto, Y.; Shô, I. Tetrahedron Lett. 1991, 32, 1975-1978.
14. (e) Furuta, T.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1992, 863-864.
15. (f) Furuta, T.; Yamamoto, Y. J. Org. Chem. 1992, 57, 2981-2982.
16. (g) Pearson, W. H.; Lindbeck, W. H.; Kampf, J. W. J. Am. Chem. Soc. 1993, 115, 2622-2636.
17. (h) Gawley, R. E.; Zhang, Q. J. Org. Chem. 1995, 60, 5763-5769.
18. (i) Gawley, R. E. Adv. Asym. Synth. 1998, 3, 77-111.
19. (a) Gaul, C.; Seebach, D. Org. Lett. 2000, 2, 1501-1504.
20. (b) Gawley, R. H.; Zhang, Q.; McPhail, A. T. Tetrahedron: Asymmetry 2000, 11, 2093-2106.
21. (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
22. (b) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451-454.
23. Coldham, I.; Holman, S.; Lang-Anderson, M. M. S. J. Chem. Soc., Perkin Trans. 1 1997, 1481-1485.
24. (a) Ortiz, J.; Guijarro, A.; Yus, M. An. Quim. Int. Ed. 1997, 93, 44-48.
25. (b) Ponzo, V. L.; Kaufman, T. Can. J. Chem. 1998, 76, 1338-1343.
26. Presented, in part, at the 221st American Chemical Society annual meeting, April 1-5 2001, San Diego, CA; Abstract ORGN523.
27. Still, W. C. J. Am. Chem. Soc. 1978, 100, 1481-1487.
28. Koppenhoefer, B.; Schurig, V. Organic Syntheses; Heathcock, C. H., Ed.; John Wiley & Sons: New York, 1988; Vol. 66, pp 160-172.
29. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983; pp 5-20.
30. Determined by comparison of retention times on a chiral HPLC column (Chiralcel OD) using authentic commercial samples.
31. (a) Fraenkel, G.; Henrichs, M.; Hewitt, J. M.; Su, B. M.; Geckle, M. J. J. Am. Chem. Soc. 1980, 102, 3345-3350.
32. (b) Seebach, D.; Hässig, R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308-337.
33. (c) Fraenkel, G.; Henrichs, M.; Hewitt, M.; Su, B. M. J. Am. Chem. Soc. 1984, 106, 255-256.
34. (d) McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805-1810.
35. (e) McGarrity, J. F.; Ogle, C. A.; Brich, Z.; Loosli, H.-R. J. Am. Chem. Soc. 1985, 107, 1810-1815.
36. (f) Williard, P. G.; Sun, C. J. Am. Chem. Soc. 1997, 119, 11693-11694.
37. Reich, H. J.; Phillips, N. H. J. Am. Chem. Soc. 1986, 108, 2102-2103.
38. Sawyer, J. S.; Kucerovy, A.; Macdonald, T. L.; McGarvey, G. J. J. Am. Chem. Soc. 1988, 110, 842-853.