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Boultwood T, Bull JA. Stereospecific functionalization of iodoaziridines via unstabilized aziridinyllithiums generated by iodine-lithium exchange. Org Lett. 2014;16(10):2740-3doi: 10.1021/ol501024y.
Boultwood, T., & Bull, J. A. (2014). Stereospecific functionalization of iodoaziridines via unstabilized aziridinyllithiums generated by iodine-lithium exchange. Organic letters, 16(10), 2740-3. https://doi.org/10.1021/ol501024y
Boultwood, Tom, and Bull, James A. "Stereospecific functionalization of iodoaziridines via unstabilized aziridinyllithiums generated by iodine-lithium exchange." Organic letters vol. 16,10 (2014): 2740-3. doi: https://doi.org/10.1021/ol501024y
Boultwood T, Bull JA. Stereospecific functionalization of iodoaziridines via unstabilized aziridinyllithiums generated by iodine-lithium exchange. Org Lett. 2014 May 16;16(10):2740-3. doi: 10.1021/ol501024y. Epub 2014 May 01. PMID: 24786465.
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Org Lett. 2014 May 16;16(10):2740-3. doi: 10.1021/ol501024y. Epub 2014 May 01.

Stereospecific functionalization of iodoaziridines via unstabilized aziridinyllithiums generated by iodine-lithium exchange.

Organic letters

Tom Boultwood, James A Bull

Affiliations

  1. Department of Chemistry, Imperial College London , South Kensington, London SW7 2AZ, U.K.

PMID: 24786465 DOI: 10.1021/ol501024y

Abstract

Lithium-iodine exchange on alkyl- or aryl-substituted N-tosyliodoaziridines afforded unstabilized aziridinyllithiums, which were subsequently trapped at low temperatures with a range of carbon and heteroatom electrophiles affording cis-substituted aziridines exclusively. When using isocyanates as electrophiles, access to aziridine carboxamides or 1,3,5-trisubstituted hydantoins can be selected by control of reaction temperature.

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