Synthesis of fused-ring and attached-ring bis-tetrahydrofurans via Pd-catalyzed carboetherification.
A five step-synthesis of fused bis-tetrahydrofurans and attached bis-tetrahydrofurans from butadiene diepoxide is described. Two sequential Pd-catalyzed carboetherification reactions between protected 1,2-diols and aryl/alkenyl bromides, each of which form both a C-O bond and a C-C bond, are used to generate the heterocyclic rings with >20:1 dr. Installation of different R(1) and R(2) groups is achieved in a straightforward fashion through use of different aryl or alkenyl bromide coupling partners.
Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, USA.
Amanda F
AF
Ward
John P
JP
Wolfe
D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D005663:Furans; D006842:Hydrocarbons, Brominated; D010165:Palladium