Enantioselective syntheses of ring-C precursors of vitamin B12. Substrate control. A novel Si-assisted elimination of vinyl bromides.
Homochiral ring-C precursors 34 of Vitamin B(12) have been prepared by Ireland-Claisen rearrangement of allyl esters 32, followed by a novel Si-assisted elimination of HBr. [reaction: see text]
Jacobi
Peter A
PA
Burke Chemical Laboratory, Dartmouth College, Hanover, New Hampshire 03755, USA. peter.a.jacobi@dartmouth.edu
Tassa
Carlos
C
D001965:Bromides / Q000737:chemistry*; D015394:Molecular Structure; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism; D014805:Vitamin B 12 / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D001965:Bromides; D014805:Vitamin B 12; D012825:Silicon