Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 23, Pages 11637-11645Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo401489q
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Funding
- University of Toronto
- Government of Ontario
- NSERC
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Vicinal aziridine-containing diamines have been obtained with high syn-stereoselectivity from readily available aziridine aldehyde dimers in the Petasis borono-Mannich reaction. Subsequent solvent- and/or nucleophile-dependent ring-opening of the aziridine ring yields functionalized 1,2- and 1,3-diamines with high regioselectivity. The ring opening is also influenced by the substitution at the C3 position of the aziridine. A mechanistic rationale for the highly syn-selective three-component reaction is proposed.
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