Homologation of boronic esters with lithiated epoxides for the stereocontrolled synthesis of 1,2- and 1,3-diols and 1,2,4-triols.
Lithiated epoxides react stereospecifically with boronic esters to give syn-1,2-diols, a process that can be used iteratively to create triols containing four stereogenic centers.
Vedrenne
Emeline
E
School of Chemistry, University of Bristol, Bristol BS81TS, UK.
Wallner
Olov A
OA
Vitale
Maxime
M
Schmidt
Frank
F
Aggarwal
Varinder K
VK
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D001897:Boronic Acids; D004852:Epoxy Compounds; D004952:Esters; D009942:Organometallic Compounds; D008094:Lithium