Tandem Wittig rearrangement/aldol reactions for the synthesis of glycolate aldols

Organic Letters

Volumn 8, Issue 20, 2006, Pages 4661-4663

  Bertrand, Myra Beaudoin ^a   Wolfe, John P ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; GLYCOLIC ACID; GLYCOLIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALDEHYDES; GLYCOLATES;

EID: 33750087308     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062016l     Document Type: Article

References (24)

1. Wittig, G.; Löhmann, L. Liebigs Ann. 1942, 550, 260.
2. (a) Tomooka, K.; Yamamoto, H.; Nakai, T. Liebigs Ann./Recueil 1997, 1275.
3. (b) Tomooka, K. In The Chemistry of Organolithium Compounds; Rappoport, Z., Marek, I., Eds.; Wiley: London, 2004; Vol. 2, pp 749-828.
4. For examples of [1,2]-Wittig rearrangements in the context of complex molecule synthesis, see: (a) Tomooka, K.; Yamamoto, H.; Nakai, T. Angew. Chem., Int. Ed. 2000, 39, 4500.
5. (b) Tomooka, K.; Kikuchi, M.; Igawa, K.; Suzuki, M.; Keong, P.-H.; Nakai, T. Angew. Chem., Int. Ed. 2000, 39, 4502.
6. (c) Schreiber, S. L.; Goulet, M. T.; Schulte, G. J. Am. Chem. Soc. 1987, 109, 4718.
7. Boron aldol reactions of methyl O-benzyl glycolate with aliphatic aldehydes proceed at -78 °C without rearrangement. See: Sugano, Y.; Naruto, S. Chem. Pharm. Bull. 1989, 37, 840.
8. For a one-step, three-component synthesis of glycolate aldol products bearing tertiary alcohols, see: Nicewicz, D. A.; Johnson, J. S. J. Am. Chem, Soc. 2005, 127, 6170.
9. (a) Trost, B. M.; Probst, G. D.; Schoop, A. J. Am. Chem. Soc. 1998, 120, 9228.
10. (b) Hecker, S. J.; Werner, K. J. Org. Chem. 1993, 58, 1762.
11. For examples of [1,2]-Wittig rearrangements of etiolates, see: (a) Curtin, D. Y.; Proops, W. R. J. Am. Chem. Soc. 1954, 76, 494.
12. (b) Paquette, L. A.; Zeng, Q. Tetrahedron Lett. 1999, 40, 3823.
13. (c) Vilotijevic, I.; Yang, J.; Hilmey, D.; Paquette, L. A. Synthesis 2003, 1872.
14. (d) Garbi, A.; Allain, L.; Chorki, F.; Ourevitch, M.; Crousse, B.; Bonnet-Delpon, D.; Nakai, T.; Begue, J.-P. Org. Lett. 2001, 3, 2529.
15. For examples of [2,3]-Wittig rearrangements of boron ester enolates, see: (a) Oh, T.; Wrobel, Z.; Rubenstein, S. M. Tetrahedron Lett. 1991, 32, 4647.
16. (b) Fujimoto, K.; Matsuhashi, C.; Nakai, T. Heterocycles 1996, 42, 423.
17. Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169.
18. Aldol reactions of O-protected 2-hydroxycarbonyl compounds that afford tertiary alcohol products also generally proceed with modest diastereoselectivity unless BHT esters or chiral auxiliaries are employed. See: (a) Murata, Y.; Kamino, T.; Hosokawa, S.; Kobayashi, S. Tetrahedron Lett. 2002, 43, 8121.
19. (b) Kamino, T.; Murata, Y.; Kawai, N.; Hosokawa, S.; Kobayashi, S. Tetrahedron Lett. 2001, 42, 5249.
20. (c) Montgomery, S. H.; Pirrung, M. C.; Heathcock, C. H. Carbohydr. Res. 1990, 202, 13.
21. (d) Heathcock, C. H.; Pirrung, M. C.; Young, S. D.; Hagen, J. P.; Jarvi, E. T.; Badertscher, U.; Märki, H.-P.; Montgomery, S. H. J. Am. Chem. Soc. 1984, 106, 8161.
22. Ester 2 was prepared through an aldol reaction between acrolein and the lithium enolate of 1 at -78 °C.
23. 2BOTf were unsuccessful. Boron-mediated aldol reactions of unprotected glycolate esters have also not been described in the literature. This suggests that 7 is not an intermediate along the reaction pathway and that formation of enolate 6 from borylated ester 5 occurs more rapidly than protonolysis of 5 to afford 7.
24. 1H NMR nOe analysis of an acetonide derivative of 3. See the Supporting Information for complete details.