Tandem aldol-Tishchenko reactions of lithium enolates: A highly stereoselective method for diol and triol synthesis

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 5674-5675

  Bodnar, Paul M ^a   Shaw, Jared T ^a   Woerpel, K A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ACETALDEHYDE; ACETIC ACID DERIVATIVE; BENZALDEHYDE; BENZOIC ACID ESTER DERIVATIVE; ESTER DERIVATIVE; GLYCOL; KETONE DERIVATIVE; LITHIUM; PROPIOPHENONE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0030870018     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971012e     Document Type: Article

References (27)

1. (1)(a) For a recent review of stereoselective aldol reactions, see: Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317-338.
2. (b) For a review of lithium enolate aldol reactions, see: Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 181-238.
3. Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066-1081.
4. For recent investigations of aldol reactions employing lithium enolates, see: Evans, D. A.; Yang, M. G.; Dart, M. J.; Duffy, J. L. Tetrahedron Lett. 1996, 37, 1957-1960 and references cited therein.
5. Baramee, A.; Chaichit, N.; Intawee, P.; Thebtaranonth, C.; Thebtaranonth, Y. J. Chem. Soc., Chem. Commun. 1991, 1016-1017.
6. Horiuchi, Y.; Taniguchi, M.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1995, 36, 5353-5356.
7. (a) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447-6449.
8. (b) The method reported by Evans and Hoveyda has been applied to the synthesis of rapamycin: Romo, D.; Meyer, S. D.; Johnson, D. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 7906-7907.
9. In a synthesis of zaragozic acid A, Heathcock observed diol monoesters when lithium enolates were treated with excess aldehyde: Caron, S.; Stoermer, D.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9126-9134.
10. For a related transformation, see: Molander, G. A.; McKie, J. A. J. Am. Chem. Soc. 1993, 115, 5821-5822.
11. Other isolated examples of this reaction have been observed for other metal enolates. (a) Zinc: ref 5. (b) Samarium: Curran, D. P.; Wolin, R. L. Synlett 1991, 317-318. (c) Nickel: Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30-44.
12. Other isolated examples of this reaction have been observed for other metal enolates. (a) Zinc: ref 5. (b) Samarium: Curran, D. P.; Wolin, R. L. Synlett 1991, 317-318. (c) Nickel: Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30-44.
13. Other isolated examples of this reaction have been observed for other metal enolates. (a) Zinc: ref 5. (b) Samarium: Curran, D. P.; Wolin, R. L. Synlett 1991, 317-318. (c) Nickel: Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30-44.
14. Recently, Mahrwald reported a titanium-catalyzed tandem aldol-Tishchenko reaction involving 3-pentanone and aldehydes: Mahrwald, R.; Costisella, B. Synthesis 1996, 1087-1089.
15. The utility of tandem reactions in synthesis has been discussed; see, for example: (a) Tietze, L. F. Chem. Rev. 1996, 96, 115-136. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
16. The utility of tandem reactions in synthesis has been discussed; see, for example: (a) Tietze, L. F. Chem. Rev. 1996, 96, 115-136. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
17. (a) Bodnar, P. M.; Palmer, W. S.; Shaw, J. T.; Smitrovich, J. H.; Sonnenberg, J. D.; Presley, A. L.; Woerpel, K. A. J. Am. Chem. Soc. 1995, 117, 10575-10576.
18. (b) Bodnar, P. M.; Palmer, W. S.; Ridgway, B. H.; Shaw, J. T.; Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1997, 62, 4737-4745.
19. 3: C, 71.97; H, 8.86. Found: C, 72.07; H, 8.81.
20. Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511-3515.
21. Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099-7100.
22. The details are provided as Supporting Information.
23. (a) Hamana, H.; Sasakura, K.; Sugasawa, T. Chem. Lett. 1984, 1729-1732.
24. (b) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871-6874.
25. Brown, H. C.; Dhar, R. K.; Bakshi, R. K.; Pandiarajan, P. K.; Singaram, B. J. Am. Chem. Soc. 1989, 111, 3441-3442.
26. Wu, Y.-D.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 906-908.
27. 2CHO is likely to occur with little stereoselectivity at the newly formed hemiacetal stereocenter. Only one diastereomer of 7 is capable of undergoing hydride transfer by the six-membered transition state 8.