South African Journal of Chemistry
On-line version ISSN 1996-840X
Print version ISSN 0379-4350
BOYLE, Grant A.; GOVENDER, Thavendran; KRUGER, Hendrik G. and MAGUIRE, Glenn E.M.. Synthesis of novel 3-hydroxy-3-pyridylcamphor derivatives. S.Afr.j.chem. (Online) [online]. 2009, vol.62, pp.113-123. ISSN 1996-840X.
The synthesis of a series of five novel precursor compounds derived from (R)-(+)-camphor is reported. From these precursors, a further four novel pyridyl alcohol ligands were synthesized. The molecules represent the first reported examples where the pyridyl and hydroxyl moieties are pendant on the C3 position of the camphor skeleton. The regioselective synthesis was investigated and an efficient method was identified. The final ligands were obtained in moderate yield with absolute regio- and stereoselective control. The molecules were screened as catalysts in the alkylation of aldehydes with diethylzinc in order to compare the new arrangement of donor groups with previously reported results obtained with C2 pendant ligands. The results demonstrated a significant improvement for the synthesized C3 pendant ligands over previous C2 examples with moderate yields and up to 85 % ee being obtained.
Keywords : Chiral; camphor ligands; pyridyl alcohols; asymmetric alkylation reactions.