DMAP-promoted racemization-free deacylation of carboxthioimide† adducts: carboxthioimide as a versatile carboxy protecting group
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Dah-Wei Su, Ying-Chuan Wang and Tu-Hsin Yan
Abstract
The DMAP-promoted deacylation of carboxthioimide adducts can be directed to form either acid or various ester protecting groups with no detectable levels of epimerization.
References
Selected reviews: D. A. Evans, J. V. Nelson and T. R. Taber, Top. Stereochem., 1982, 13, 1 Search PubMed; C. H. Heathcock, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, New York, 1984, vol. 3, p. 111 Search PubMed.
D. A. Evans, J. Bartrol and T. L. Shih, J. Am. Chem. Soc., 1981, 103, 2127 CrossRefCAS.
A. Abdel-Magid, N. P. Lendon, S. E. Drake and L. Ivan, J. Am. Chem. Soc., 1986, 108, 4595 CrossRefCAS.
H. Heathcock, Aldrichim. Acta, 1990, 23, 99 Search PubMed and references cited therein M. P. Bonner and E. R. Thornton, J. Am. Chem. Soc., 1991, 113, 1299 Search PubMed; Y.-C. Wang, A.-W. Hung, C.-S. Chang and T.-H. Yan, J. Org. Chem., 1996, 61, 2038 CrossRefCAS.
T.-H. Yan, C.-W. Tan, H.-C. Lee, H.-C. Lo and T.-Y. Huang, J. Am. Chem. Soc., 1993, 115, 2613 CrossRefCAS; T.-H. Yan, A.-W. Hung, H.-C. Lee and C.-S. Chang, J. Org. Chem., 1994, 59, 8187 CrossRefCAS; T.-H. Yan, A.-W. Hung, H.-C. Lee, C.-S. Chang and W.-H. Liu, J. Org. Chem., 195, 60, 3301 Search PubMed.
C.-N. Hsiao, L. Liu and M. J. Miller, J. Org. Chem., 1987, 52, 2201 CrossRefCAS.
D. A. Evans, M. D. Ennis and D. J. Mathre, J. Am. Chem. Soc., 1982, 104, 1737 CrossRefCAS; D. A. Evans, M. M. Morrissey and R. L. Dorow, J. Am. Chem. Soc., 1985, 107, 4346 CrossRefCAS; D. A. Evans, J. A. Ellman and R. L. Dorow, Tetrahedron Lett., 1987, 28, 1123 CrossRefCAS; D. A. Evans, T. C. Britton and J. A. Ellman, Tetrahedron Lett., 1987, 28, 6141 CrossRefCAS.
G. Hofle, W. Steglich and H. Vorbruggen, Angew. Chem., Int. Ed. Engl., 1978, 17, 569 CrossRef; B. Neises and W. Steglich, Angew. Chem., Int. Ed. Engl., 1978, 17, 522 CrossRef.
D. A. Evans, K. T. Chapman and J. Bisaha, J. Am. Chem. Soc., 1988, 110, 1238 CrossRefCAS.
D. A. Evans, S. J. Miller and T. Lectka, J. Am. Chem. Soc., 1993, 115, 6460 CrossRefCAS.
New compounds have been satisfactorily characterized spectroscopically, and elemental composition has been established by high-resolution mass spectroscopy and/or combustion analysis.
Amino Acids, Peptides and Proteins, Specialist Periodical Reports, vol. 1–16, ed. G. T. Young and R. C. Sheppard, Chemistry Society, London, 1968–1983 Search PubMed; T. Sunazuka, T. Nagamitsu, K. Matsuzaki, H. Tanaka, S. Omura and A. B. Smith, III, J. Am. Chem. Soc., 1993, 115, 5302 Search PubMed.
D. A. Evans, E. B. Sjogren, A. E. Weber and R. E. Conn, Tetrahedron Lett., 1987, 28, 39 CrossRefCAS; E. J. Corey, D.-H. Lee and S. Choi, Tetrahedron Lett., 1992, 33, 6735 CrossRefCAS.
Prepared from the TiCl4-mediated aldolization of camphor-based 3-bromoacetyl-1,3-oxazolidine-2-thione with isobutyraldehyde.
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