Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Asymmetric Induction in C-Alkylation of Tropane-Derived Enamines: Congruence Between Computation and Experiment

Asymmetric Induction in C-Alkylation of Tropane-Derived Enamines: Congruence Between Computation and Experiment
Kelvin E. Jackson, Amber L. Thompson, Asma Khurshid, Andrew Charlton, Yifei Li, Robert S. Paton, Heinrich-K. A. Rudy, David. M. Hodgson, Ben Le Neve-Foster
Quantum chemical studies of C-ethylation of 1-methyl- and 1,4,4-trimethyl-tropane-derived enamines predict good (89:11 er, B3LYP) and high (98:2 er, B3LYP) levels, respectively, of asymmetric induction in the resulting α-alkylated aldehydes. The nonracemic tropanes were synthesized using Mannich cyclization strategies (Robinson-Schöpf and by way of a Davis-type N-sulfinyl amino bisketal, respectively), and ethylation of the derived enamines was found to support the predicted sense and magnitude of asymmetric induction (81:19 er and 95:5 er, respectively). A comparison of several computational methods highlights the robustness of predicted trends in enantioselectivity, enabling theory to guide synthesis.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01954

DOI: 10.1021/acs.joc.7b01954

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