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. Author manuscript; available in PMC: 2020 Aug 5.
Published in final edited form as: Tetrahedron. 2019 May 1;75(24):3309–3318. doi: 10.1016/j.tet.2019.04.060

Table 2.

Optimization of ring closing metathesis on macrocycle precursors 8c and 8d, which contain Z alkenes.

graphic file with name nihms-1529178-t0003.jpg
Entry RCM precursor Catalyst Solvent T(°C) Yield
1 8c [Ru]-1 (20 mmol%) Tol 23 -a
2 8c [Ru]-2 (20 mmol%) Tol 23 25%b
3 8c [Ru]-3 (20 mmol%) Tol 23 -a
4 8c [Ru]-4 (20 mmol%) Tol 23 38%b
5 8c [Ru]-5 (20 mmol%) Tol 23 -a
6 8c [Ru]-6 (20 mmol%) Tol 23 -a
7 8c [Ru]-7 (20 mmol%) Tol 23 27%b
8 8c [Ru]-4 (8 mmol%) × 2 Tol 23 40%b
9 8c [Ru]-4 (8 mmol%) × 2 BTF 23 42%b
10 8c [Ru]-8 (8 mmol%) × 2 BTF 23 33%b
11 8c [Ru]-9 (8 mmol%) × 2 BTF 0 -a
12 8c [Ru]-10 (8 mmol%) × 2 BTF 23 28%b
13 8c [Ru]-11 (8mmol%) × 2 BTF 23 49%c
14 8d [Ru]-11 (8 mmol%) × 2 DCM 23 72%c
a.

No product detected.

b.

Yield determined by 1H NMR analysis of the crude reaction mixture using 1,4-dinitrobenzene as an internal standard.

c.

isolated yield after column chromatography. BTF = benzotrifluoride, DCM = dichloromethane, Tol = toluene.