Remote exo/endo selectivity in selective monohydrolysis of dialkyl bicyclo[2.2.1]heptane-2,3-dicarboxylate derivatives.
High exo-facial selectivity was observed in the selective monohydrolysis of a series of near-symmetric diesters that possess an exo-ester group and an endo-ester group attached on a norbornane or norbornene skeleton. The selectivities were found to be clear-cut, although the reaction center in these reactions is one covalent bond distant from the norbornane or norbornene ring, where the difference of the environment between the exo face and endo face is therefore expected to be negligible. The effect of the co-solvent we studied earlier for the selective monohydrolysis reaction was also confirmed and contributed to improvement of the yields of the half-esters.
Niwayama
Satomi
S
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA. satomi.niwayama@ttu.edu
Cho
Hanjoung
H
Zabet-Moghaddam
Masoud
M
Whittlesey
Bruce R
BR
D002264:Carboxylic Acids / Q000737:chemistry*; D006536:Heptanes / Q000737:chemistry*; D006868:Hydrolysis; D009636:Norbornanes / Q000737:chemistry; D012997:Solvents
D002264:Carboxylic Acids; D006536:Heptanes; D009636:Norbornanes; D012997:Solvents