Tandem regio- and stereoselective organocuprate-mediated bis-allylic substitutions.
anti-5-Acetoxy-4-halo-alpha,beta-enoates undergo sequential or tandem reactions with two different magnesium cuprate reagents to afford anti-2,3-dialkyl-4,5-enoates in high chemical yield and with excellent diastereoselectivity. The one-pot tandem procedure can be achieved with 30 mol % of CuCN and affords a rapid stereoselective combinatorial approach to vicinal disubstituted gamma,delta-enoates containing functionality at either end of the carbon chain for subsequent functional group elaboration. The methodology should provide a powerful practical strategy for acyclic stereoselection.
Dieter
R Karl
RK
Hunter Laboratory, Department of Chemistry, Clemson University, Clemson, South Carolina 29634-0973, USA. dieterr@clemson.edu
Guo
Fenghai
F
D000498:Allyl Compounds / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000498:Allyl Compounds; D004952:Esters; D009942:Organometallic Compounds; D003300:Copper; D008274:Magnesium