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. Author manuscript; available in PMC: 2021 Oct 1.
Published in final edited form as: Tetrahedron Lett. 2020 Aug 16;61(40):152333. doi: 10.1016/j.tetlet.2020.152333

Table 2.

Cycloisomerization of 1820: variation of R under a variety of conditions.

Entry Substrate Conditionsa Time Conversionb
1 18 1, + AgOTf, 70 °C 1 h 15%
1, + AgOTf, 70 °C 16 h 99%
2 18 2 + AgOTf, 70 °C 1 h 7%
2 + AgOTf, 70 °C 16 h 99%
3 19 1, + AgOTf, 70 °C 1 h 0%
1, + AgOTf, 70 °C 16 h 50%
4 19 2 + AgOTf, 70 °C 1 h 0%
2 + AgOTf, 70 °C 16 h 37%
5 20 1, + AgOTf, 70 °C 16 h 0%
a

[Substrate] = 0.04 mM, [Au] = 0.002 mM (0.05 mol%) [additive] = 0.004 mM (0.1 mol%), reaction volume 0.60 mL.

b

As determined by NMR integration, all species were cleanly resolved, the only observable compounds were starting [Substrate] or product 26.