Pinacol Cross Coupling Reactions of Ethyl 2-Alkyl-2-Formylpropionates. Stereoselective Synthesis of 2,2,4-Trialkyl-3-Hydroxy-γ-Butyrolactones

Synlett

Volumn 1997, Issue 1, 1997, Pages 41-43

  Kang, Min ^a   Park, Jeonghan ^a   Pedersen, Steven F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041366897     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-709     Document Type: Article

References (23)

1. Park, J.; Pedersen, S. F. J. Org. Chem. 1990, 55, 5924.
2. Yamago, S.; Machii, D.; Nakamura, E. J. Org. Chem. 1991, 56, 2098 and references therein.
3. Starting with 2a, pinacol cross coupling reactions provide an attractive alternative to well documented aldol reactions between enolates of isobutyric acid derviatives and α-alkoxy aldehydes: (a) Arrastia, I.; Lecea, B.; Cossio, F. P. Tet. Lett. 1996, 37, 245. (b) Takebuchi, K.; Hamada, Y.; Shioiri, T. Tet. Lett. 1994, 35, 5239.
4. Starting with 2a, pinacol cross coupling reactions provide an attractive alternative to well documented aldol reactions between enolates of isobutyric acid derviatives and α-alkoxy aldehydes: (a) Arrastia, I.; Lecea, B.; Cossio, F. P. Tet. Lett. 1996, 37, 245. (b) Takebuchi, K.; Hamada, Y.; Shioiri, T. Tet. Lett. 1994, 35, 5239.
5. 4, and evaporated to give a foam. The foam was dissolved in 20 mL of benzene; 5 mg of para-toluenesulfonic acid (PTSA) was added and the reaction was stirred for 1-2 h. The mixture was concentrated and the residue was purified by chromatography on silica gel using an eluent of ethyl acetate in hexane to give 6.
6. 1H NMR spectra are consistent with calculated coupling constants (Jaime, C.; Segura, C.; Dinares, I.; Font, J. J. Org. Chem. 1993, 58, 154). In all other cases the stereochemistry is inferred based on the established stereochemisties of 6c,e,f.
7. (a) Freudenherger, J. H.; Konradi, A. W.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 8014.
8. (b) Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1990, 55, 4506.
9. (c) Konradi, A. W.; Pedersen, S. F. ibid. 1992, 57, 28.
10. (d) Kraynack, E.; Pedersen, S. F. ibid. 1993, 58, 6114.
11. (e) Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316.
12. To our knowledge, diastereofacial selective additions of this magnitude to a prochiral carbonyl bearing three non-hydrogen α-substituents, two of which are methyl and ethyl, is without precedent except for the chemistry described in ref. 1. For examples of chelation-controlled addition reactions to α-hydroxy (or alkoxy) carbonyls bearing two different non-hydrogen substituents, see: (a) Reetz, M. T.; Steinbach, R.; Westermann, J.; Urz, R.; Wenderoth, B.; Peter, R. Angew. Chem. Int. Ed. Engl. 1982, 21, 135. (b) Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748. (c) Cram, D. J.; Allinger, J. ibid. 1954, 76, 4516. (d) Cram, D. J.; Elhafez, F. A. A. ibid. 1952, 74, 5828. For an additional example related to this area see: Reetz, M. T. Nach. Chem. Tech. Lab. 1981, 29, 165.
13. To our knowledge, diastereofacial selective additions of this magnitude to a prochiral carbonyl bearing three non-hydrogen α-substituents, two of which are methyl and ethyl, is without precedent except for the chemistry described in ref. 1. For examples of chelation-controlled addition reactions to α-hydroxy (or alkoxy) carbonyls bearing two different non-hydrogen substituents, see: (a) Reetz, M. T.; Steinbach, R.; Westermann, J.; Urz, R.; Wenderoth, B.; Peter, R. Angew. Chem. Int. Ed. Engl. 1982, 21, 135. (b) Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748. (c) Cram, D. J.; Allinger, J. ibid. 1954, 76, 4516. (d) Cram, D. J.; Elhafez, F. A. A. ibid. 1952, 74, 5828. For an additional example related to this area see: Reetz, M. T. Nach. Chem. Tech. Lab. 1981, 29, 165.
14. To our knowledge, diastereofacial selective additions of this magnitude to a prochiral carbonyl bearing three non-hydrogen α-substituents, two of which are methyl and ethyl, is without precedent except for the chemistry described in ref. 1. For examples of chelation-controlled addition reactions to α-hydroxy (or alkoxy) carbonyls bearing two different non-hydrogen substituents, see: (a) Reetz, M. T.; Steinbach, R.; Westermann, J.; Urz, R.; Wenderoth, B.; Peter, R. Angew. Chem. Int. Ed. Engl. 1982, 21, 135. (b) Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748. (c) Cram, D. J.; Allinger, J. ibid. 1954, 76, 4516. (d) Cram, D. J.; Elhafez, F. A. A. ibid. 1952, 74, 5828. For an additional example related to this area see: Reetz, M. T. Nach. Chem. Tech. Lab. 1981, 29, 165.
15. To our knowledge, diastereofacial selective additions of this magnitude to a prochiral carbonyl bearing three non-hydrogen α-substituents, two of which are methyl and ethyl, is without precedent except for the chemistry described in ref. 1. For examples of chelation-controlled addition reactions to α-hydroxy (or alkoxy) carbonyls bearing two different non-hydrogen substituents, see: (a) Reetz, M. T.; Steinbach, R.; Westermann, J.; Urz, R.; Wenderoth, B.; Peter, R. Angew. Chem. Int. Ed. Engl. 1982, 21, 135. (b) Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748. (c) Cram, D. J.; Allinger, J. ibid. 1954, 76, 4516. (d) Cram, D. J.; Elhafez, F. A. A. ibid. 1952, 74, 5828. For an additional example related to this area see: Reetz, M. T. Nach. Chem. Tech. Lab. 1981, 29, 165.
16. To our knowledge, diastereofacial selective additions of this magnitude to a prochiral carbonyl bearing three non-hydrogen α-substituents, two of which are methyl and ethyl, is without precedent except for the chemistry described in ref. 1. For examples of chelation-controlled addition reactions to α-hydroxy (or alkoxy) carbonyls bearing two different non-hydrogen substituents, see: (a) Reetz, M. T.; Steinbach, R.; Westermann, J.; Urz, R.; Wenderoth, B.; Peter, R. Angew. Chem. Int. Ed. Engl. 1982, 21, 135. (b) Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748. (c) Cram, D. J.; Allinger, J. ibid. 1954, 76, 4516. (d) Cram, D. J.; Elhafez, F. A. A. ibid. 1952, 74, 5828. For an additional example related to this area see: Reetz, M. T. Nach. Chem. Tech. Lab. 1981, 29, 165.
17. For reviews of chelation-controlled addition reactions see: (a) Reetz, M. T. Accts. Chem. Res. 1993, 26, 462. (b) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer Verlag: Berlin, 1986. (c) Reetz, M. T. Angew. Chem. Int. Ed. Engl. 1984, 23, 556.
18. For reviews of chelation-controlled addition reactions see: (a) Reetz, M. T. Accts. Chem. Res. 1993, 26, 462. (b) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer Verlag: Berlin, 1986. (c) Reetz, M. T. Angew. Chem. Int. Ed. Engl. 1984, 23, 556.
19. For reviews of chelation-controlled addition reactions see: (a) Reetz, M. T. Accts. Chem. Res. 1993, 26, 462. (b) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer Verlag: Berlin, 1986. (c) Reetz, M. T. Angew. Chem. Int. Ed. Engl. 1984, 23, 556.
20. It is known that 3c can function as a chelating aldehyde (using the pyranose oxygen) in reactions with methyl magnesium bromide (ref. 8c). However, we have found that this aldehyde does not function in this manner when forced to compete with the strongly chelating substrates 1 and 2.
21. For pertinent references and a discussion, see, Lodge, E. P.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 3353.
22. Renaud, P.; Hurzeler, M.; Seebach, D. Helv. Chim. Acta 1987, 70, 292.
23. f 0.43.