Figure 4: Evaluating the potential of this strategy to address synthetically relevant problems. | Nature Communications

Figure 4: Evaluating the potential of this strategy to address synthetically relevant problems.

From: Asymmetric trapping of zwitterionic intermediates by sulphur ylides in a palladium-catalysed decarboxylation-cycloaddition sequence

Figure 4

(a) Gram-scale reaction. (b,c) Application of the cross-metathesis (CM) reaction to introduce other substituents at the end of a terminal alkene. (d,e) Derivatization of chiral indoline product 3a. (f) Synthetic significance of the oxazolo[3,4-a]indol-3-one core. Reagents and conditions: (i) NaBH4 (4 equiv.), MeOH, 0 °C, 30 min, then room temperature (r.t.), 2 h; (ii) NaH (1.5 equiv.), propargyl bromide (1.3 equiv.), THF, r.t., 5 h; (iii) Co2(CO)8 (0.3 equiv.), TMTU (1.2 equiv.), CO (1 atm), toluene, 65 °C, 4 h; (iv) Mg (powder, 10 equiv.), MeOH, N2, 12 h; (V) CDI (1.1 equiv.), DCM, r.t., 12 h. TMTU: tetramethyl thiourea; CDI: di(1H-imidazol-1-yl)methanone.

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