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. Author manuscript; available in PMC: 2011 Jun 9.
Published in final edited form as: J Am Chem Soc. 2010 Jun 9;132(22):7645–7655. doi: 10.1021/ja910290c

Table 3.

Au-Catalyzed Cycloisomerization of Homopropargyl Ketones 6

graphic file with name nihms207351t13.jpg

Entry Substrate Product 2, %a,b
1 graphic file with name nihms207351t14.jpg graphic file with name nihms207351t15.jpg 2f, 79
2 graphic file with name nihms207351t16.jpg graphic file with name nihms207351t17.jpg 2g, 91
3 graphic file with name nihms207351t18.jpg graphic file with name nihms207351t19.jpg 2h, 91c
4 graphic file with name nihms207351t20.jpg graphic file with name nihms207351t21.jpg 2i, 48d
5 graphic file with name nihms207351t22.jpg graphic file with name nihms207351t23.jpg 2j, 65e
6 graphic file with name nihms207351t24.jpg graphic file with name nihms207351t25.jpg 2k, 71f
7 graphic file with name nihms207351t26.jpg graphic file with name nihms207351t27.jpg 2l, 68
8 graphic file with name nihms207351t28.jpg graphic file with name nihms207351t29.jpg 2m, 77
9 graphic file with name nihms207351t30.jpg graphic file with name nihms207351t31.jpg 2n, 67
a

Isolated yield of product for reactions performed on 0.5 mmol scale.

b

2f and 2l contained 8 and 6% of the corresponding desilylated furan, respectively.

c

14:1 ratio of 2h:3h.

d

10:1 ratio of 2i:3i.

e

8:1 ratio of 2j:3j.

f

GC Yield, 2k is a volatile compound.