N-acyl-5,5-dimethyl-oxazolidin-2-ones as latent aldehyde equivalents

Tetrahedron Letters

Volumn 40, Issue 36, 1999, Pages 6677-6680

  Bach, Jordi ^a   Bull, Steven D ^a   Davies, Stephen G ^a   Nicholson, Rebecca L ^a   Sanganee, Hitesh J ^a   Smith, Andrew D ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBOXYLIC ACID DERIVATIVE; OXAZOLIDINONE DERIVATIVE;

ACYLATION; ARTICLE; CHELATION; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; DECOMPOSITION; HYDROLYSIS; OXIDATION; REDUCTION;

EID: 0033520268     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01345-3     Document Type: Article

References (17)

1. (a) Evans, D. A.; Ng, H. P. Tetrahedron Lett., 1993, 34, 14, 2229;
2. (b) Hori, K.; Hikage, N.; Inagaki, A.; Mori, S.; Nomura, K.; Yoshii, E. J. Org. Chem. 1992, 57, 2888;
3. (c) Evans, D. A.; Polniaszek, R. P.; DeVries, K. M.; Guinn, D. E.; Mahre, D. J. J. Am. Chem. Soc., 1991, 113, 7613;
4. (d) Andersen, M. W.; Hildebrandt, B.; Dahmann, G.; Hoffmann, R. W. Chem. Ber., 1991, 124, 2127;
5. (e) Jones, T. K.; Reamer, R. A.; Desmond, R.; Mills, S. G. J. Am. Chem. Soc., 1990, 112, 2998.
6. For leading references see Larock, R. C. Comprehensive Organic Transformations, VCH: New York, 1989; Chandrasekar, S.; Kumar, M. S.; Muralidhar, B. Tetrahedron. Lett., 1998, 39, 909; Nahm, S.; Weinreb, S. M. Tetrahedron Lett., 1981, 22, 39, 3815; Sibi, M. P. Org. Prep. Proced. Int., 1993, 25, 15; Mentzel, M.; Hoffman, H. M. R. J. Prakt. Chem., 1997, 339, 517
7. For leading references see Larock, R. C. Comprehensive Organic Transformations, VCH: New York, 1989; Chandrasekar, S.; Kumar, M. S.; Muralidhar, B. Tetrahedron. Lett., 1998, 39, 909; Nahm, S.; Weinreb, S. M. Tetrahedron Lett., 1981, 22, 39, 3815; Sibi, M. P. Org. Prep. Proced. Int., 1993, 25, 15; Mentzel, M.; Hoffman, H. M. R. J. Prakt. Chem., 1997, 339, 517
8. For leading references see Larock, R. C. Comprehensive Organic Transformations, VCH: New York, 1989; Chandrasekar, S.; Kumar, M. S.; Muralidhar, B. Tetrahedron. Lett., 1998, 39, 909; Nahm, S.; Weinreb, S. M. Tetrahedron Lett., 1981, 22, 39, 3815; Sibi, M. P. Org. Prep. Proced. Int., 1993, 25, 15; Mentzel, M.; Hoffman, H. M. R. J. Prakt. Chem., 1997, 339, 517
9. For leading references see Larock, R. C. Comprehensive Organic Transformations, VCH: New York, 1989; Chandrasekar, S.; Kumar, M. S.; Muralidhar, B. Tetrahedron. Lett., 1998, 39, 909; Nahm, S.; Weinreb, S. M. Tetrahedron Lett., 1981, 22, 39, 3815; Sibi, M. P. Org. Prep. Proced. Int., 1993, 25, 15; Mentzel, M.; Hoffman, H. M. R. J. Prakt. Chem., 1997, 339, 517
10. For leading references see Larock, R. C. Comprehensive Organic Transformations, VCH: New York, 1989; Chandrasekar, S.; Kumar, M. S.; Muralidhar, B. Tetrahedron. Lett., 1998, 39, 909; Nahm, S.; Weinreb, S. M. Tetrahedron Lett., 1981, 22, 39, 3815; Sibi, M. P. Org. Prep. Proced. Int., 1993, 25, 15; Mentzel, M.; Hoffman, H. M. R. J. Prakt. Chem., 1997, 339, 517
11. While oxazolidin-2-thiones have been shown to exhibit the cleavage properties of Weinreb amides, to the best of our knowledge there are no reports on the use of oxazolidin-2-ones to this end. (a) Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fusita, E. J. Org. Chem., 1986, 51, 2391;
12. (b) Izawa, T.; Mukaiyama, T.; Bull. Chem. Soc. Jpn., 1979, 52, 2, 555.
13. (a) Bull, S. D.; Davies, S. G.; Jones, S.; Sanganee, H. J. J. Chem. Soc. Perkin Trans.1, 1999, 387
14. (b). Bull, S. D.; Davies, S. G.; Jones, S.; Polywka, M. E. C.; Prasad, R. S.; Sanganee, H. J. Synlett, 1998, 519;
15. (c) Davies, S. G.; Sanganee H. J. Tetrahedron: Asymmetry, 1995, 6, 671.
16. Evans, D. A.; Dow, R. L.; Shih, T. L.; Takacs, J. M.; Zahler R. J. Am. Chem. Soc., 1990, 112, 5290.
17. 1H (400MHz) NMR spectroscopic analysis of the crude reaction mixture and could easily be separated to homogeneity by column chromatography.