Organic Letters
Organic Letters
5 years ago

Carbon–Nitrogen Bond Formation via the Vanadium Oxo Catalyzed Sigmatropic Functionalization of Allenols

Carbon–Nitrogen Bond Formation via the Vanadium Oxo Catalyzed Sigmatropic Functionalization of Allenols
Jacob S. Tracy, Barry M. Trost
A vanadium catalyzed 1,3-rearrangement of allenols to form transient vanadium enolates that selectively couple with electrophilic nitrogen sources is reported even in the presence of competing simple protonation and Alder-ene pathways. Hydrazine products can be cyclized in a 6-endo-trig fashion which, upon reductive cleavage of the N–N bond, yield 1,4-diamines. Additionally, cleavage of the N–N bond before cyclization can be achieved to form β-hydroxy amines, a common structural motif of biologically active compounds.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00961

DOI: 10.1021/acs.orglett.7b00961

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