Undergraduate Research Symposium

The synthesis of chiral ligands for transition metal catalysts is vital to developing catalytic reactions with high enantioselectivity. This work discusses progress toward the synthesis of a novel chiral ferrocene ligand. The final product is formed from a β-ketoacyl ferrocene whose synthesis has been reported,1 and previous experiments have shown that the α-alkyl group can easily be added. However, the addition of the diphenylphosphine requires deprotonation of the cyclopentadienyl ring.2 When the β-ketoacyl or acetyl group is present, the addition of a base leads to a facile aldol condensation. To circumvent this, instead of phosphorylating the β-ketoacylferrocene, acetylferrocene was successfully protected as a thioacetal using propan-1,3-dithiol3 in order to carry out the phosphorylation reaction, and the β-ketoacyl group will be added in a later step. Our efforts to carry out the phosphorylation, deprotection, and further elaboration of the ferrocenyl framework will be described.