An efficient and general synthesis of homochiral alpha-amino substituted bromo-heteroaromatics B using a diastereoselective 1,2-addition has been developed. The obtained heteroaromatic intermediates allow for a rapid two-dimensional exploration of a new series of histone deacetylase inhibitors, through Suzuki-Miyaura cross-coupling reactions for the introduction of a second aromatic element, followed by global deprotection and derivatization of the amino group. (C) 2009 Published by Elsevier Ltd.
Schultz-Fademrecht, C., Kinzel, O., Marko, I., Pospisil, T., Pesci, S., Rowley, M., & Jones, P. (2009). A general approach to homochiral alpha-amino substituted bromo-heteroaromatics suitable for two-dimensional rapid analogue synthesis. Tetrahedron, 65(45), 9487-9493. https://doi.org/10.1016/j.tet.2009.08.013 (Original work published 2009)