Organic Chemistry, Short talk
OC-025

Stereodivergent Catalyst Control of Two Stereogenic Axes

D. Moser1, C. Sparr1*
1University of Basel

The implications of stereoisomerism on biological activity is well known and versatile methods for their selective synthesis is hence required. Most molecules important to life have multiple stereogenic moieties and catalyst-control over diastereomers is therefore particular relevant. The simultaneous creation of more than one stereocenter in a single synthetic step is thus highly desirable and provides the basis for straightforward and short routes to complexes molecular scaffolds. Our group recently developed an iterative method for the catalyst-controlled stereodivergent synthesis of atropisomeric multiaxis systems.[1]We now present a stereodivergent diastereo- and enantioselective method with simultaneous catalyst-control over two stereogenic axes. Along with controllable syn- or anti-configuration, the products show useful levels of enantiopurity. The structurally well-defined scaffolds bear two stereogenic axes and are envisioned to provide ligands, catalysts and molecular building blocks.[2]

[1] D. Lotter, A.Castrogiovanni, M. Neuburger, C. Sparr,  ACS Cent. Sci., 2018, 4, 656-660.
[2] D.Moser, C. Sparr, unpublished results.