Article citationsMore>>

Dean, M.A. and Hitchcock, S.R. (2010) Synthesis and Application of Oxadiazines as Chiral Ligands for the Enantioselective Addition of Diethylzinc to Aldehydes. Tetrahedron: Asymmetry, 21, 2471-2478.
https://doi.org/10.1016/j.tetasy.2010.09.010

has been cited by the following article:

• TITLE: Chiral Camphor-Based 1,3- and 1,4-Amino Alcohols and Aminodiols as Ligands for Diethylzinc Addition to Aldehydes

  AUTHORS: Olusegun B. Olubanwo, James A. Golen, Arnold L. Rheingold, Vesa Nevalainen

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

  JOURNAL NAME: International Journal of Organic Chemistry, Vol.8 No.2, June 22, 2018

  ABSTRACT: 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.