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. Author manuscript; available in PMC: 2009 Nov 6.
Published in final edited form as: Org Lett. 2008 Oct 11;10(21):5091–5094. doi: 10.1021/ol802147h

Table 1.

Scope of alkynyl ether sythesis via elimination of enol triflatesa

graphic file with name nihms86409t1.jpg
entry R1 R2 3 (% yield) 5 5 (% yield)
1 Ph menthyl 91 a 75
2 Ph CH2CH(CH2)3 89 b 82
3 Ph t-Bu 67 c 68
4 Ph Ph 78 d 70
5 1-cyclohexenyl menthyl 84 e 90
6 (CH3)2CCH CH2CH(CH2)3 81 f 68
7 PhCC menthyl 69b g 64
8 t-Bu CH2CH(CH2)3 87 h --c
9 C6H13 menthyl 90 i --c
a

Reaction conditions: a. R2OH (1.5 equiv), In(OTf)3 (10 mol %), toluene, rt; b. LiHMDS, THF, −78 °C, then PhNTf2, DMPU, −78 °C-rt; c. KOt-Bu, THF, −78 °C.

b

Yield of 3g prepared in three steps from menthol via an alternative route described in the text.

c

No alkynyl ethers were detected in the reaction mixture; see text for details.