Convergent synthesis of stereodefined exo-alkylidene-gamma-lactams from beta-halo allylic alcohols.
A convergent process for the assembly of stereodefined mono- and bicyclic exo-alkylidene-gamma-lactams is described that proceeds through the union of beta-halo allylic alcohols, aromatic imines, and CO. Overall, regio- and stereoselective Ti-mediated reductive cross-coupling, followed by Pd-catalyzed carbonylation, can be performed in a one- or two-pot procedure, defining a highly selective three-component coupling process for heterocycle synthesis.
Umemura
Shuhei
S
Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA.
McLaughlin
Martin
M
Micalizio
Glenn C
GC
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007097:Imines / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
D007097:Imines; D007769:Lactams; D020005:Propanols; C006463:allyl alcohol; D010165:Palladium