fig2

Synthesis of chiral <i>spiro</i>-indenes via Pd-catalyzed asymmetric (4 + 2) dipolar cyclization

Figure 2. Condition optimization. Conditions: 1a (0.1 mmol), 2a (0.2 mmol), Pd2(dba)3·CHCl3 (5 mol%) and chiral ligand (20 mol%) in 2.0 mL anhydrous DCM at rt under the irradiation of 6 W blue LEDs for 24 h. aDetermined by analyzing the 1H NMR of reaction mixture with 1,3,5-trimethoxybenzene as an internal standard. bDetermined by chiral HPLC analysis of the purified products. cDetermined by 1H NMR analysis of the reaction mixture. dLigand (10 mol%) was used instead. eIsolated yield. dba: Dibenzylideneacetone; rt: room temperature; LEDs: light-emitting diodes; dr: diastereoisomer ratio; ee: enantiomer excess; DCM: dichloromethane; ND: not detected; DMF: N,N-dimethylformamide; THF: tetrahydrofuran; NMR: nuclear magnetic resonance; HPLC: high performance liquid chromatography.

Chemical Synthesis
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