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. Author manuscript; available in PMC: 2012 Jun 1.
Published in final edited form as: Org Biomol Chem. 2011 Oct 19;10(1):56–59. doi: 10.1039/c1ob06189e

Table 2.

Ring closing metathesis on cycloheptenones to generate bi- and tricyclic products.a

graphic file with name nihms377543u2.jpg
entry substrate (1) R1 product (17) yield (%)b
1c 1h graphic file with name nihms377543t11.jpg graphic file with name nihms377543t12.jpg
17a
17b
R2 = H 93
2 1i graphic file with name nihms377543t13.jpg R2 =
graphic file with name nihms377543t14.jpg
99
3d 1c graphic file with name nihms377543t15.jpg graphic file with name nihms377543t16.jpg
17c
17d
R2 = H 91
4d 1d graphic file with name nihms377543t17.jpg R2 = Me 90
5 1e graphic file with name nihms377543t18.jpg graphic file with name nihms377543t19.jpg
17e
17f
R2 = H 90
6 1f graphic file with name nihms377543t20.jpg R2= Me 98
7e 1j graphic file with name nihms377543t21.jpg graphic file with name nihms377543t22.jpg
17g
96
8 1g graphic file with name nihms377543t23.jpg graphic file with name nihms377543t24.jpg
17h
99
a

Conditions: cycloheptenone 1 (1.0 equiv) and Grubbs–Hoveyda 2nd generation catalyst (5.0 mol %) in benzene, 50 °C.

b

Yield of isolated product.

c

See Supporting Information for alternative reaction parameters.

d

1,4-benzoquinone (10 mol %) added.

e

Performed in toluene.