HMPA promotes retro-aldol reaction, resulting in syn-selective addition of lithiated 1-naphthylacetonitrile to aromatic aldehydes

Organic Letters

Volumn 2, Issue 16, 2000, Pages 2443-2445

  Carlier, Paul R ^a,b   Lo, Cedric W S ^b   Lo, Michael M C ^b   Wan, Nan Chi ^b   Williams, Ian D ^b  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000526031     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006099w     Document Type: Article

References (19)

1. Dykstra, R. R. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1995; Vol. 4; pp 2668-2675.
2. (a) Ireland, R. E.; Mueller, R. H.; Williard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2877.
3. (b) Ireland, R. E.; Wipf, P.; Armstrong, J. D., III. J. Org. Chem. 1991, 56, 650-657.
4. Xie, L.; Saunders, W. H., Jr. J. Am. Chem. Soc. 1991, 113, 3123-3130.
5. Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751-5757.
6. Fataftah, Z. A.; Kopka, I. E.; Ratke, M. W. J. Am. Chem. Soc. 1980, 102, 3959-3960.
7. (a) Brown, C. A.; Yamaichi, A. J. Chem. Soc., Chem. Commun. 1979, 100-101.
8. (b) Binns, M. R.; Haynes, R. K. J. Org. Chem. 1981, 46, 3790-3795.
9. Reich, H. J.; Sikorski, W. H. J. Org. Chem. 1999, 64, 14-15.
10. Luchetti, J.; Krief, A. Tetrahedron Lett. 1978, 30, 2697-2700.
11. For the use of a chiral phosphoramide catalyst to reverse the kinetic diastereoselectivity of addition of trichlorosilylenol ethers to aldehydes, see: Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334.
12. Carlier, P. R.; Lo, K.-M.; Lo, M. M.-C.; Williams, I. D. J. Org. Chem. 1995, 60, 7511-7517.
13. Thus far HMPA is uniquely effective. In reactions of 4 and 5a, LiCl, DMSO, TMEDA, and the HMPA substitutes DMPU and dimethylacetamide failed to induce syn-selectivity. Use of sodium hexamethylsilazide as base, with or without added HMPA, resulted in poor syn-selectivity.
14. Carlier, P. R.; Lo, K.-M.; Lo, M. M-C.; Lo, P. C.-K.; Lo, C. W.-S. J. Org. Chem. 1997, 62, 6316-6321.
15. Carlier, P. R.; Lo, K.-M. J. Org. Chem. 1994, 59, 4053-4055.
16. Carlier, P. R.; Lam, W. W.-F.; Wan, N.-C.; Williams, I. D. Angew. Chem. Int. Ed. 1998, 37, 2252-2254.
17. Heathcock, C. H.; Lampe, J. J. Org. Chem. 1983, 48, 4330-4337.
18. (a) Kleschick, W. A.; Buse, C. T.; Heathcock, C. H. J. Am. Chem. Soc. 1977, 99, 247-248.
19. (b) Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066-1081