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. 2023 Mar 14;14(14):3907–3912. doi: 10.1039/d2sc06664e

Advanced substrates for direct chloriranium-induced terpene cyclizationa.

Entry Substrate Product Yieldb (d.r.)
1 graphic file with name d2sc06664e-u3.jpg graphic file with name d2sc06664e-u4.jpg 25% (>95 : 5)
2 graphic file with name d2sc06664e-u5.jpg graphic file with name d2sc06664e-u6.jpg 51% (73 : 27)
3c graphic file with name d2sc06664e-u7.jpg graphic file with name d2sc06664e-u8.jpg 40% (>95 : 5)
a

Substrate (0.20 mmol, 1.0 eq.) was added to 76.8 mg reagent 21 (0.24 mmol, 1.2 eq.) and 7.33 mg saccharin 22 (40 μmol, 0.2 eq.) in 2.00 mL HFIP at 0 °C.

b

Isolated yield.

c

2.4 eq. reagent 21 was used. The d.r. was determined by 1H-NMR spectroscopy of the crude reaction mixture. The given d.r. refers to the configuration at the carbon(s) highlighted in grey.