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Issue 21, 2013
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The asymmetric synthesis of terminal aziridines by methylene transfer from sulfonium ylides to imines

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Abstract

A new ylide-based protocol for the asymmetric aziridination of imines via methylene transfer has been developed involving the use of a simple chiral sulfonium salt and an organic strong base. A systematic study identified triisopropylphenyl sulfonylimines as optimal substrates for the process. Unexpectedly, hindered C2-symmetric sulfonyl salts incorporating bulky ethers at C-2 and C-5 – which had previously been useful in the corresponding epoxidation chemistry – decomposed in these aziridination reactions via competing elimination pathways. Under optimised conditions it was found that a simple salt derived from (2R,5R)-2,5-diisopropyl thiolane could mediate asymmetric methylene transfer to a range of imines with uniformly excellent yields with 19–30% ee. Since this is a similar level of enantiomeric excess to that obtained using these same salts in epoxidation chemistry, it was concluded that if more bulky sulfonium salts could be devised which were resistant to decomposition under the reaction conditions, that highly enantioselective aziridine formation by methylene transfer would be possible.

Graphical abstract: The asymmetric synthesis of terminal aziridines by methylene transfer from sulfonium ylides to imines

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Publication details

The article was received on 22 Nov 2012, accepted on 03 Apr 2013 and first published on 18 Apr 2013


Article type: Paper
DOI: 10.1039/C3OB27271K
Citation: Org. Biomol. Chem., 2013,11, 3535-3540
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    The asymmetric synthesis of terminal aziridines by methylene transfer from sulfonium ylides to imines

    S. A. Kavanagh, A. Piccinini and S. J. Connon, Org. Biomol. Chem., 2013, 11, 3535
    DOI: 10.1039/C3OB27271K

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