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. Author manuscript; available in PMC: 2009 Dec 24.
Published in final edited form as: J Am Chem Soc. 2008 Dec 24;130(51):17258–17259. doi: 10.1021/ja807894t

Table 1.

Ruthenium-catalyzed ring-expansion of silyl-substituted alkynylcyclopropanols

graphic file with name nihms91458f3.jpg
Entry R Z/E (5/6) ratioa Time(h) Yieldb
1 TMS 4a 5.7:1 2 98%
2 BDMS 4b 6.0:1 4 94%
3 SiMe2Ph 4c 6.0:1 2 96%
4 TES 4d 10.0:1 2 97%
5 TBS 4e 11.4:1 2 98%
6 TIPS 4f > 20:1 2 87%c
a

Geometry was assigned by analogy to the Z and E isomers 5a/6a: see Supporting Information for details.

b

Total yield of two isomers determined by 1H-NMR with mesitylene as internal standard.

c

Isolated yield. BDMS = benzyl(dimethyl)silyl.