Alkylation of chiral α-hydroxy ketones derived from (1R)-(+)-camphor. An asymmetric variant of the classical acetylene route to carbonyl compounds

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3249-3252

  Palomo, Claudio ^a   Oiarbide, Mikel ^a   Mielgo, Antonia ^a   González, Alberto ^b   García, Jesús M ^b   Landa, Cristina ^b   Lecumberri, Ainara ^b   Linden, Anthony ^c  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b PUBLIC UNIVERSITY OF NAVARRE   (Spain)

^c UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041524978     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0163530     Document Type: Article

References (35)

1. (a) Stereoselective Synthesis (Houben-Weyl), E21 Vol. 2; Helmchen, G., Hoffmann, R. W., Mulzer J., Shaumann, E., Eds., Georg Thieme: Stuttgart, New York, 1996.
2. (b) Fey, P.; Hartwig, W. In ref 1a, pp 969-972.
3. (c) Enders, D. In Asymmetric Synthesis, Vol. 3B; Morrison, J. D., Ed.; Academic Press: Orlando, 1984; p.275.
4. (d) Enders, D.; Kipphardt, H.; Fey, P. Organic Syntheses; Wiley: New York, 1993; Collect. Vol. VIII, pp 403-414.
5. (e) Enders, D.; Klatt, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; p 178.
6. (f) Fey, P. In ref 1a, pp 973-1015. For enantioselcctivc enolate alkylations, see:
7. (g) O'Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439-1457.
8. (h) Hughes, D. L. In Comprehensive Asymmetric Catalysis III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Heidelberg, 1999; pp 1273-1294.
9. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley: New York, 1995; pp 166-187.
10. For reviews, see: (a) Rück, K. Angew. Chem., Int. Ed. Engl. 1995, 34, 433-435.
11. (b) Franklin, A. S. J. Chem. Soc., Perkin Trans. 1 1998, 2451-2465.
12. (c) Regan, A. C. J. Chem. Soc., Perkin Trans. 1 1998, 1151-1166.
13. (d) Regan, A. C. J. Chem. Soc., Perkin Trans. 1 1999, 357-373.
14. (e) Fey, P. In ref 1a, pp 1016-1029. For a recent practical example, see:
15. (f) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511.
16. For industrial applications of acetylene, see: (a) Weissermel, K.; Arpe, H.-J. Industrial Organic Chemistry; VCH: Weinheim, 1997; pp 91-104.
17. (b) Szmant, H. H. Organic Building Blocks of the Chemical Industry; John Wiley: New York, 1989; pp 188-264.
18. For a recent innovative approach to transform alkynes into carbonyls with an α stereogenic center, see: (a) Spino, C.; Beaulieu; C. J. Am. Chem. Soc. 1998, 120, 11832-11833.
19. (b) Spino, C.; Beaulieu, C.; Lafreniere, J. J. Org. Chem. 2000, 65, 7091-7097.
20. (a) Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Linden, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 180-182.
21. (b) Palomo, C.; Oiarbide, M.; Aizpurua, J. M.; González, A.; García, J. M.; Landa, C.; Odriozola, I.; Linden, A. J. Org. Chem. 1999, 64, 8193-8200.
22. Palomo, C.; Oiarbide, M.; González-Rego, M. C.; Sharma, A. K.; García, J. M.; González, A.; Landa, C.; Linden, A. Angew. Chem., Int. Ed. 2000, 39, 1063-1065.
23. A small amount (2%-4%) of the starting unreacted methyl ketone 2 was isolated in some instances.
24. For the problem of stereocontrol in enolate methylations, see, for instance: (a) Evans, D. A.; Chapman, K. T.; Hung, D. T.; Kawaguchi, A. T. Angew. Chem., Int. Ed. Engl. 1987, 26, 1184-1186.
25. (b) Palomo, C.; Berrée, F.; Linden. A.; Villalgordo, J. M. J. Chem. Soc., Chem. Commun. 1994, 1861-1862.
26. (c) Boyd, V. A.; Perales, J. B.; Negrete, G. R. Tetrahedron Lett. 1997, 38, 6631-6634.
27. (d) Abdel-Aziz, A. A.-M.; Okuno, J.; Tanaka, S.; Ishizuka, T.; Matsunaga, H.; Kunieda, T. Tetrahedron Lett. 2000, 41, 8533-8537.
28. 4, and the solvent was removed under reduced pressure. The alkylated products were obtained as white solids or oils. Diatereomeric ratios were determined by gas chromatography. Purification was effected by silica gel flash column chromatography (eluant: ethyl acetate/hexane 1:30).
29. D = +41.5 (c = 1.0 in EtOH).
30. 2) [published value for the (S)-isomer +19 (neat) [Aldrich catalog]].
31. 2) [published value for the (S)-isomer +19 (neat) [Aldrich catalog]].
32. Crystallographic data (excluding structure factors) for the structures 19b and 19c reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as suplemmentary publication numbers CCDC-161732 and 161733, respectively. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax (+44) 1223 336-033; e-mail deposit@ccdc.cam.ac.uk).
33. For a recent example, see: Oppolzer, W.; Darcel, C.; Rochet, P.; Rosset, S.; deBrabander, J. Helv. Chim. Acta 1997, 80, 1319-1337.
34. For the problems associated with the alkylation of open-chain ketones, see: ref 2, p 168.
35. The enantiomeric purity of carboxylic acids 25, 26, and 27 was determined by HPLC analyses of their methyl esters using a ChiralCel OB-H column and hexanes as the eluant (flow 0.5 mL/min). The same method was applied for the determination of the enantiomeric purity of ketones 28, 29, and 30, and it was confirmed by comparison of the chromatograms with those corresponding to racemic products.