Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH13464
RESEARCH ARTICLE
Contents Vol 67(3)

Selective Cleavage of Carbamate Protecting Groups from Aziridines with Otera’s Catalyst

Shan Sun A , Ilaria Tirotta A , Nicholas Zia A and Craig A. Hutton A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Melbourne, Vic. 3010, Australia.

B Corresponding author. Email: chutton@unimelb.edu.au

Australian Journal of Chemistry 67(3) 411-415 https://doi.org/10.1071/CH13464
Submitted: 3 September 2013  Accepted: 16 October 2013   Published: 11 November 2013

Abstract

Otera’s distannoxane catalyst was found to promote the cleavage of carbamate groups from N-protected aziridines. This method enables the chemoselective cleavage of an aziridinyl N-carbobenzyloxy (Cbz) group in the presence of other N-Cbz groups. The selectivity is due to the longer, weaker N–C bond of aziridinyl carbamates, as inferred through IR and crystallographic analyses.


References

[1]     (a) P. G. M. Wuts, T. W. Greene, Greene’s Protective Groups in Organic Synthesis, 4th edn 2007 (John Wiley & Sons: Hoboken, NJ).
         (b) P. Kocienski, Protecting Groups, 3rd edn 2005 (Georg Thieme Verlag: Stuttgart).

[2]  (a) J. Otera, Chem. Rev. 1993, 93, 1449.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXktVyisb8%3D&md5=c645463e3a1a6468b4850900eed8d858CAS |
      (b) J. Otera, N. Dan-oh, H. Nozaki, J. Org. Chem. 1991, 56, 5307.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  I. Tirotta, N. L. Fifer, J. Eakins, C. A. Hutton, Tetrahedron Lett. 2013, 54, 618.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhsF2htw%3D%3D&md5=edfd456c712ee1ab94a06d989a73cf23CAS |

[4]  The low isolated yields of unprotected aziridines following work-up and chromatography may reflect the inherent instability of these compounds; see Ref. [10].

[5]  Y.-C. Wu, J. Zhu, Org. Lett. 2009, 11, 5558.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtlyht7rE&md5=3821e880cceeeff794760091d7109452CAS | 19894720PubMed |

[6]  D. R. Langley, D. E. Thurston, J. Org. Chem. 1987, 52, 91.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2sXms12rtg%3D%3D&md5=e2315ddd7f7e25a7f7ac4b9adbe4b350CAS |

[7]  P. Barraclough, P. Dieterich, C. A. Spray, D. W. Young, Org. Biomol. Chem. 2006, 4, 1483.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xkt1Kht7k%3D&md5=26cd16337966947add407ef332580ca5CAS | 16604215PubMed |

[8]  P. Huy, H.-G. Schmalz, Synthesis 2011, 954.
         | 1:CAS:528:DC%2BC3MXltlKgtbc%3D&md5=2197a2ff464d6b4d22bddc397d6de69eCAS |

[9]  Z. Bernstein, D. Ben-Ishai, Tetrahedron 1977, 33, 881.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2sXlsFWru7Y%3D&md5=ffce19d6203c1aeaaa4bf1ba7450369eCAS |

[10]  A. Korn, S. Rudolph-Boehner, L. Moroder, Tetrahedron 1994, 50, 1717.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXlvVSitL4%3D&md5=ab07469eecee1d2b47cd69f4e0f10a61CAS |

[11]  D. Williams, I. Fleming, Spectroscopic Methods in Organic Chemistry, 6th edn 2007 (McGraw-Hill Book Company: London).

[12]  Search of CSD for carbamate-protected aziridines conducted on 19 July 2013, removing bicyclic examples.

[13]  S. Minakata, Y. Murakami, R. Tsuruoka, S. Kitanaka, M. Komatsu, Chem. Commun. 2008, 6363.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsVKgs77I&md5=87eacee27d7eb7af64ff26740d43407bCAS |

[14]  A. L. Braga, P. H. Schneider, M. W. Paixão, A. M. Deobald, C. Peppe, P. Bottega, J. Org. Chem. 2006, 71, 4305.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XjslKltb4%3D&md5=e38372eeec33016638acf2fa1258bc16CAS | 16709076PubMed |

[15]  C. W. West, M. A. Estiarte, D. H. Rich, Org. Lett. 2001, 3, 1205.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXhvFaqtb0%3D&md5=09ce23ecf2d0e49935b50561f47d7680CAS | 11348195PubMed |

[16]  R. G. Vaswani, A. R. Chamberlin, J. Org. Chem. 2008, 73, 1661.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtFShsbs%3D&md5=639bb785d8efbb4aae58362aa61c4d9fCAS | 18225916PubMed |

[17]  N. Floyd, B. Vijayakrishnan, J. R. Koeppe, B. G. Davis, Angew. Chem. Int. Ed. 2009, 48, 7798.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1ektL%2FN&md5=7af1c39cddef7931f751323745122f77CAS |

[18]  J. C. Lanter, S. Zhang, B. Zhao, PCT patent WO01/04091A1 2001.

[19]  T. D. Penning, G.-D. Zhu, V. B. Gandhi, J. Gong, X. Liu, Y. Shi, V. Klinghofer, E. F. Johnson, C. K. Donawho, D. J. Frost, V. Bontcheva-Diaz, J. J. Bouska, D. J. Osterling, A. M. Olson, K. C. Marsh, Y. Luo, V. L. Giranda, J. Med. Chem. 2009, 52, 514.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsFals7bL&md5=6fadeae406f75ba9f09dbd7529400e29CAS | 19143569PubMed |

[20]  A. Colomer, A. Pinazo, M. R. Infante, L. Perez, M. A. Manresa, M. P. Vinardell, M. Mitjans, J. Med. Chem. 2011, 54, 989.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXlt1Oqtw%3D%3D&md5=a5a990f9ef50ad53ef7f05f3b031f9b5CAS | 21229984PubMed |