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Beilstein J. Org. Chem. 2016, 12, 732–744, doi:10.3762/bjoc.12.73
Graphical Abstract
Figure 1: Camphor and some camphor derivatives.
Scheme 1: Formation of 2 from reaction of oxoimine 1 with amino acids (H2NCH(R)COOH: R = H, CH3, CH2Ph, CH2CH...
Figure 2: ESI mass spectrum of 2 (positive ion mode).
Figure 3: 1H NMR spectrum of 2 in CD3CN at T = −20 °C.
Figure 4: 13C NMR spectrum of 2 in CD3CN at T = −20 °C.
Figure 5: Optimized structure of 2 ((S)-3A isomer) with labeling scheme.
Figure 6: NOESY spectrum (detail) showing the cross peak between H3A and H10A (see Supporting Information File 1, Figure S6 for the full s...
Figure 7: Upper row: anion 3 and zwitterion 4 which are stable upon geometry optimization. Middle row: zwitte...
Figure 8: Intramolecular reactions of non-zwitterionic ground state 6g to 11 (top) or 8 (bottom). The activat...
Figure 9: Transition-state geometry and salient bond distances along the IRC path for the reaction of 6g → 11...
Figure 10: Transition-state geometry and salient bond distances along the IRC path for the reaction of 6g → 8....
Figure 11: Potential products 7–11 of the Strecker degradation together with the reaction of compound 10 to gi...
Figure 12: ESI(+) tandem mass spectrum of the intermediate 12 (m/z 229) and proposed fragment ions.