Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2016 Jun 1;7(6):3775-3779.
doi: 10.1039/c5sc04151a. Epub 2016 Feb 23.

Asymmetric [3 + 2] cycloaddition of donor-acceptor aziridines with aldehydes via carbon-carbon bond cleavage

Yuting Liao  1 , Xiaohua Liu  1 , Yu Zhang  1 , Yali Xu  1 , Yong Xia  1 , Lili Lin  1 , Xiaoming Feng  1   2
Affiliations

Asymmetric [3 + 2] cycloaddition of donor-acceptor aziridines with aldehydes via carbon-carbon bond cleavage

Yuting Liao et al. Chem Sci. .

Abstract

An enantioselective [3 + 2] annulation of donor-acceptor aziridines with aldehydes has been realized using a Nd(OTf)3/N,N'-dioxide/LiNTf2 catalyst system, providing various chiral cis-1,3-oxazolidines in moderate to good yields with high levels of stereocontrol. A relay catalytic process is proposed where LiNTf2 promotes the formation of azomethine ylide intermediates, and a chiral Nd(iii)-N,N'-dioxide complex accelerates the asymmetric cycloaddition.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1. Asymmetric [3 + 2] cycloadditions of racemic aziridines.
Fig. 1
Fig. 1. (a) ee traces of the product 3kh and the substrate 1k of the reaction. (b) Reaction time profile of the reactions with or without LiNTf2.
Scheme 2
Scheme 2. Control experiments.
Scheme 3
Scheme 3. A plausible catalytic cycle.
See this image and copyright information in PMC

References

    1. For selected reviews:

    2. Ilardi E. A., Njardarson J. T. J. Org. Chem. 2013;78:9533. - PubMed
    3. Ohno H. Chem. Rev. 2014;114:7784. - PubMed
    4. Callebaut G., Meiresonne T., Kimpe N. D., Mangelinckx S., Chem. Rev., 2014, 114 , 7954 , . For recent examples . - PubMed
    5. Guo H., Xu Q., Kwon O. J. Am. Chem. Soc. 2009;131:6318. - PMC - PubMed
    6. Wender P. A., Strand D. J. Am. Chem. Soc. 2009;131:7528. - PubMed
    7. Trost B. M., Osipov M., Dong G. J. Am. Chem. Soc. 2010;132:15800. - PMC - PubMed
    8. Feng J.-J., Lin T.-Y., Wu H.-H., Zhang J. J. Am. Chem. Soc. 2015;137:3787. - PubMed
    9. Wang L., Yang D., Han F., Li D., Zhao D., Wang R. Org. Lett. 2015;17:176. - PubMed
    10. Rai A., Yadav L. D. S. Tetrahedron Lett. 2013;54:3127.
    1. Trost B. M., Fandrick D. R. J. Am. Chem. Soc. 2003;125:11836. - PubMed
    2. Xu C.-F., Zheng B.-H., Suo J.-J., Ding C.-H., Hou X.-L. Angew. Chem., Int. Ed. 2015;54:1604. - PubMed
    1. Chai Z., Zhu Y.-M., Yang P.-J., Wang S., Wang S., Liu Z., Yang G. J. Am. Chem. Soc. 2015;137:10088. - PubMed

    1. For relative reports:

    2. Huisgen R., Scheer W., Huber H. J. Am. Chem. Soc. 1967;89:1753.
    3. DoMinh T., Trozzolo A. M. J. Am. Chem. Soc. 1972;94:4046.
    4. Henke B. R., Kouklis A. J., Heathcock C. H. J. Org. Chem. 1992;57:7056.
    5. Pankova A. S., Kuznetsov M. A. Tetrahedron Lett. 2014;55:2499.

    1. For relevant examples:

    2. Pohlhaus P. D., Bowman R. K., Johnson J. S. J. Am. Chem. Soc. 2004;126:2294. - PubMed
    3. Wu X., Li L., Zhang J. Chem. Commun. 2011;47:7824. - PubMed
    4. Jiang Z., Wang J., Lu P., Wang Y. Tetrahedron. 2011;67:9609.
    5. Wu X., Zhang J. Synthesis. 2012;44:2147.
    6. Li L., Wu X., Zhang J. Chem. Commun. 2011;47:5049. - PubMed
    7. Li L., Zhang J. Org. Lett. 2011;13:5940. - PubMed
    8. Liu H., Zheng C., You S.-L. J. Org. Chem. 2014;79:1047. - PubMed
    9. Liu H., Zheng C., You S.-L. Chin. J. Chem. 2014;32:709.
    10. Ghosh A., Pandey A. K., Banerjee P. J. Org. Chem. 2015;80:7235. - PubMed
    11. Soeta T., Miyamoto Y., Fujinami S., Ukaji Y. Tetrahedron. 2014;70:6623.
    12. Craig II R. A., O'Connor N. R., Goldberg A. F. G., Stoltz B. M. Chem.–Eur. J. 2014;20:4806. - PMC - PubMed