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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 2.

Scope of alkynyl ether synthesis via elimination of enol phosphatesa

graphic file with name nihms86409t2.jpg
entry R1 R2 4 % yield 4 5 % yield 5
1 t-Bu CH2CH(CH2)3 hb 81 h 60
2 C6H13 menthyl ic 89 i 72
3 i-Pr menthyl jb 78 j 85
4 1-cyclohexenyl t-Bu kb 72 k 70
5 Ph t-Bu lb 82 c 56
a

Reaction conditions: a. KHMDS, ClPO(OR3)2, THF, 78 °C; b. n-BuLi, KOt-Bu, THF, −78 °C.

b

The diethylphosphate derivative was synthesized.

c

The diphenylphosphate derivative was synthesized.