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Generation and hydrolysis of N-acyloxazolinium salts allowing regiospecific acylation of chiral amino alcohols

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Chemistry of Heterocyclic Compounds Aims and scope

In an attempt to form 2-alkylidene-1,3-oxazolidines, chiral 2-oxazolines have been N-alkylated and N-acylated. Two new N-methyloxazolinium salts have been prepared and characterized, but alkaline treatment resulted in their decomposition. In contrast, attempts to isolate three N-benzoyloxazolinium salts gave the products of their ring hydrolysis: unsymmetrically diacylated amino alcohols whose structure was confirmed by X-ray diffraction in one case. Overall the method allows stepwise regiospecific N,O-diacylation of 2-amino alcohols.

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References

  1. Oda, M.; Morimoto, K.; Thanh, N. C.; Ohta, R.; Kuroda, S. Heterocycles2003, 60, 1673.

    Article  CAS  Google Scholar 

  2. Aitken, R. A.; Henderson, S.; Slawin, A. M. Z. J. Sulfur Chem.2018, 39, 422.

    Article  CAS  Google Scholar 

  3. Zhou, A.; Pittman, C. U., Jr. Synthesis2006, 37.

  4. Allen, P., Jr.; Ginos, J. J. Org. Chem.1963, 28, 2759.

    Article  CAS  Google Scholar 

  5. Aitken, R. A.; Armstrong, D. P.; Galt, R. H. B.; Mesher, S. T. E. J. Chem. Soc., Perkin Trans 11997, 935.

  6. Tomalia, D. A.; Paige, J. N. J. Org. Chem.1973, 38, 422.

    Article  CAS  Google Scholar 

  7. Zhou, A.; Njogu, M. N.; Pittman, C. U., Jr. Tetrahedron2006, 62, 4093.

    Article  CAS  Google Scholar 

  8. De Silva, H. I.; Song, Y.; Henry, W. P.; Pittman, C. U., Jr. Tetrahedron Lett.2012, 53, 2965.

    Article  Google Scholar 

  9. Huneck, S.; Porzel, A.; Schmidt, J.; Follmann, G. Z. Naturforsch., C: J. Biosci.1992, 47, 785.

    Article  CAS  Google Scholar 

  10. Achari, B.; Pal, A.; Pakrashi, S. C. Ind. J. Chem.1974, 12, 1218.

    CAS  Google Scholar 

  11. Naidu, P. P.; Madakka, M.; Rajesh, B. Asian J. Pharm. Clin. Res.2014, 7(Suppl. 1), 15.

    Google Scholar 

  12. Ohshima, T.; Iwasaki, T.; Maegawa, Y.; Yoshiyama, A.; Mashima, K. J. Am. Chem. Soc.2008, 130, 2944.

    Article  CAS  Google Scholar 

  13. Shibata, S.; Matsushita, H.; Kaneko, H.; Noguchi, M.; Saburi, M.; Yoshikawa, S. Bull. Chem. Soc. Jpn.1982, 55, 3546.

    Article  CAS  Google Scholar 

  14. Dalko, P. I.; Langlois, Y. J. Org. Chem.1998, 63, 8107.

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, United Kingdom

    R. Alan Aitken, Alexandra M. Z. Slawin & Andrew Wilson

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  1. R. Alan Aitken
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  2. Alexandra M. Z. Slawin
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  3. Andrew Wilson
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Correspondence to R. Alan Aitken.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(5), 611–614

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Aitken, R.A., Slawin, A.M.Z. & Wilson, A. Generation and hydrolysis of N-acyloxazolinium salts allowing regiospecific acylation of chiral amino alcohols. Chem Heterocycl Comp 56, 611–614 (2020). https://doi.org/10.1007/s10593-020-02707-3

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  • DOI: https://doi.org/10.1007/s10593-020-02707-3

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