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Beilstein J. Org. Chem. 2017, 13, 1542–1550, doi:10.3762/bjoc.13.154
Graphical Abstract
Figure 1: General uses of N-alkylcarboxyspiropyrans.
Scheme 1: C4SP–C4MC spiropyran-merocyanine equilibrium and M2+ binding.
Scheme 2: General synthesis of N-alkylcarboxyspiropyrans.
Scheme 3: Decarboxylation of N-ethanoic acid indolium salt 3a.
Scheme 4: Lactonisation of 4-bromobutyric acid 2c.
Figure 2: N-methyl spiropyran 9.
Figure 3: Example spectra illustrating binding studies of spiropyrans with M2+. (a) 1H NMR spectrum of C10SP ...
Figure 4: ε for MC–M2+ complexes of C2SP–C12SP and 9: (left) with Zn2+; (right) with Mg2+. Values for ε were ...
Figure 5: [MC] for compounds C2SP–C12SP and 9 in the presence of various metal cations. Solutions of spiropyr...
Figure 6: [MC] for spiropyrans C2SP–C12SP, 9 and 10 (0.1 mM) in CH3CN–H2O (99.9% v/v). Samples were kept in d...
Figure 7: C6 ester derivative 10.
Beilstein J. Org. Chem. 2005, 1, No. 2, doi:10.1186/1860-5397-1-2
Scheme 1:
Scheme 2:
Scheme 3:
Figure 1: Diastereoselective substitution of the N,O acetal 12
Scheme 4:
Figure 2: Diastereoselective Luche reduction of piperidinones
Scheme 5:
Figure 3: Diastereoselective dihydroxylation of unsaturated piperidines
Figure 4: Diagnostic nOe observations for the piperidine 22A
Figure 5: Diagnostic nOe observations for the piperidines 22C and 22D
Scheme 6:
Figure 6: Stereoselectivity of two-directional Luche reductions
Scheme 7:
Scheme 8:
Figure 7: Two-directional functionalisation by diastereoselective dihydroxylation