Journal article

Ring-opening hydrofluorination of 2,3- and 3,4-epoxy amines by HBF4·OEt2: application to the asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.

Abstract:: Treatment of a range of 2,3- and 3,4-epoxy amines with HBF(4)·OEt(2) at room temperature results in fast and efficient S(N)2-type ring-opening hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method. The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.

Publication status:: Published

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APA Style

Cresswell, A., Davies, S., Lee, J., Morris, M., Roberts, P., & Thomson, J. (2011). Ring-opening hydrofluorination of 2,3- and 3,4-epoxy amines by HBF4·OEt2: application to the asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol. Journal of Organic Chemistry, 76(11), 4617–4627.

MLA Style

Cresswell, A., et al. “Ring-Opening Hydrofluorination of 2,3- and 3,4-Epoxy Amines by HBF4·OEt2: Application to the Asymmetric Synthesis of (S,S)-3-Deoxy-3-Fluorosafingol.” Journal of Organic Chemistry, vol. 76, no. 11, 2011, pp. 4617–27.

Chicago Style

Cresswell, A, S Davies, J Lee, M Morris, P Roberts, and J Thomson. 2011. “Ring-Opening Hydrofluorination of 2,3- and 3,4-Epoxy Amines by HBF4·OEt2: Application to the Asymmetric Synthesis of (S,S)-3-Deoxy-3-Fluorosafingol.” Journal of Organic Chemistry 76 (11): 4617–27.
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Publisher copy:: 10.1021/jo200517w

Authors

+ Cresswell, A More by this author

Role:: Author

+ Davies, S More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Lee, J More by this author

Role:: Author

+ Morris, M More by this author

Role:: Author

+ Roberts, P More by this author

Role:: Author

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Journal:: Journal of organic chemistry More from this journal
Volume:: 76
Issue:: 11
Pages:: 4617-4627
Publication date:: 2011-06-01
DOI:: 10.1021/jo200517w
EISSN:: 1520-6904
ISSN:: 0022-3263

Language:: English
Pubs id:: pubs:138784
UUID:: uuid:52763eb7-7f58-4a50-a130-1d2e86ff8448
Local pid:: pubs:138784
Source identifiers:: 138784
Deposit date:: 2012-12-19

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Copyright date:: 2011

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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