Stereospecific Functionalization of Iodoaziridines via Unstabilized Aziridinyllithiums Generated by Iodine–Lithium Exchange | Zendy

Tom Boultwood | Zendy; James A. Bull | Zendy

Open Access

Stereospecific Functionalization of Iodoaziridines via Unstabilized Aziridinyllithiums Generated by Iodine–Lithium Exchange

Author(s) -

Tom Boultwood,

James A. Bull

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol501024y

Subject(s) - chemistry , electrophile , lithium (medication) , aryl , stereospecificity , aziridine , heteroatom , surface modification , iodine , alkyl , electrophilic substitution , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis , ring (chemistry) , medicine , endocrinology

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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