Barry M Trost1, Jacob S Tracy1. 1. Department of Chemistry, Stanford University , 333 Campus Drive, Stanford, California 94305, United States.
Abstract
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.
A vanadium catalyzed 1,3-rearrangement of n class="Chemical">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.
Authors: Michel Muehlebach; Manfred Boeger; Fredrik Cederbaum; Derek Cornes; Adrian A Friedmann; Jutta Glock; Thierry Niderman; André Stoller; Trixie Wagner Journal: Bioorg Med Chem Date: 2009-01-03 Impact factor: 3.641