Pure Appl. Chem., 2013, Vol. 85, No. 4, pp. 701-720
http://dx.doi.org/10.1351/PAC-CON-12-06-04
Published online 2012-10-12
Use of sulfur fragments for the synthesis of nitrogen heterocycles
Abstract:
This contribution contains a representative sampling from the Padwa laboratory of the conjugate addition of oximes with 2,3-bis(phenylsulfonyl)-1,3-butadiene followed by a subsequent dipolar cycloaddition cascade to produce a variety of alkaloids. The resulting cycloadducts are cleaved reductively to provide azapolycyclic scaffolds with strategically placed functionality for further manipulation of the target compounds.
Keywords
heterocyclic chemistry; nitrogen; organic synthesis; rearrangements; sulfur; tandem reactions.