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. Author manuscript; available in PMC: 2020 Jul 24.
Published in final edited form as: J Am Chem Soc. 2019 Jul 11;141(29):11414–11419. doi: 10.1021/jacs.9b05556

Figure 2:

Figure 2:

(A) Proposed catalytic cycle. Observed first order dependence on 1-Cbz and Nuc indicate that nucleophilic addition is the rate-determining step. (B) Concerted SN2 and stepwise SN1 mechanisms require different mechanisms for enantioinduction. (C) Computational evaluation of the uncatalyzed reaction predicts that the SN1 pathway is much higher in energy than the SN2 pathway. All DFT calculations were performed at the B3LYP-D3(BJ)/6-311+G(d,p) level of theory including solvent corrections PCM(DCM). For a fuller discussion of the computational study, see SI.