Journal article

Publication year: 2011

Pages: 9764-9776

Journal: The Journal of Organic Chemistry

Volume number: 76

Issue number: 23

DOI Link: https://doi.org/10.1021/jo201864e

Publisher: American Chemical Society

Abstract: 

We report a new thiourea–Brønsted acid cooperative catalytic system for
the enantioselective cyanosilylation of aldehydes with yields up to 90%
and enantioselectivities up to 88%. The addition of an achiral acid was
found to be crucial for high asymmetric induction. Mechanistic
investigations using a combination of NMR, ESI-MS, and density
functional theory computations (including solvent corrections) at the
M06/6-31G(d,p) level of theory suggest that the key catalytic species
results from the cooperative interaction of bifunctional thioureas and
an achiral acid that form well-defined chiral hydrogen-bonding
environments.

Harvard Citation style: Zhang, Z., Lippert, K., Hausmann, H., Kotke, M. and Schreiner, P. (2011) Cooperative Thiourea–Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN, The Journal of Organic Chemistry, 76(23), pp. 9764-9776. https://doi.org/10.1021/jo201864e

APA Citation style: Zhang, Z., Lippert, K., Hausmann, H., Kotke, M., & Schreiner, P. (2011). Cooperative Thiourea–Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN. The Journal of Organic Chemistry. 76(23), 9764-9776. https://doi.org/10.1021/jo201864e