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. Author manuscript; available in PMC: 2012 May 20.
Published in final edited form as: Org Lett. 2011 Apr 14;13(10):2586–2589. doi: 10.1021/ol200697m

Table 1.

ddition of Phenols to Activated Allenesa

graphic file with name nihms-288843-t0003.jpg
entry R1 R2 E 1 yield (%)b E:Zc
1 H H CO2Et 1a >99 E only
2 4-Me H CO2Et 1b 97 E only
3 4-OMe H CO2Et 1c 92 E only
4 4-I H CO2Et 1d 69 E only
5 4-Br H CO2Et 1e 72 E only
6 4-Cl H CO2Et 1f 62 E only
7 4-F H CO2Et 1g 78 E only
8 4-CF3 H CO2Et 1h 73 E only
9 4-CO2Et H CO2Et 1i 90 E only
10 4-NHBoc H CO2Et 1j 89 4:1
11 3-Me H CO2Et 1k 95 E only
12 2-Me H CO2Et 1l 96 20:1
13 2-I H CO2Et 1m 91 E only
14 2,6-di-Me H CO2Et 1n 66 E only
15 2,6-di-t-Bu H CO2Et 1o 0 N/A
16 4-OMe Ph CO2Et 1p 89 Z only
17 4-CF3 Ph CO2Et 1q 97 Z only
18 4-CF3 Ph CN 1r 88 Z only
a

Reactions were performed using 1.1 equiv of allene.

b

Isolated yield.

c

Determined through 1H NMR spectroscopic analysis.