Author(s)

Olusegun B. Olubanwo^1*, James A. Golen¹, Arnold L. Rheingold², Vesa Nevalainen^1,3

¹Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, North Dartmouth, USA.
²Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, USA.
³Chemveda Life Sciences, Weymouth, USA.

Syntheses of (1R,2S,3R,4S)-1,7,7-trimethyl-2-pyridin-2-ylmethylbicyclo[2.2.1]-heptane-2,3-diol (7), (1R,2S,3R,4S)-1,7,7-trimethyl-2-[(6-methyl)-pyridin-2-ylmethyl-bicyclo-[2.2.1]heptane-2,3-diol (13), and (1R,2S,2’R,4R)-1,7,7-trimethyl-2-piperidin-2-ylmethyl-bicyclo[2.2.1]heptan-2-ol (19b) from commercially available (d)-camphor (1) are described. Key steps of the syntheses involved substrate-controlled diastereoselective alkylation and platinum oxide-catalyzed hydrogenation reactions. These compounds, and other intermediate amino alcohols in their syntheses, were successfully utilized as ligands in enantioselective diethyl zinc (Et₂Zn) addition to benzaldehyde with moderate enantioselectivity.

Ligand, Enantioselective, Amino Alcohol, Aminodiols, (+)-Camphor

Olubanwo, O. , Golen, J. , Rheingold, A. and Nevalainen, V. (2018) Chiral Camphor-Based 1,3- and 1,4-Amino Alcohols and Aminodiols as Ligands for Diethylzinc Addition to Aldehydes. International Journal of Organic Chemistry, 8, 240-263. doi: 10.4236/ijoc.2018.82018.