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. Author manuscript; available in PMC: 2011 Jun 1.
Published in final edited form as: Tetrahedron. 2010 Jun;66(26):4760–4768. doi: 10.1016/j.tet.2010.03.044

Table 2.

Vinylogous Wittig reactions between the allenoate 1 and the aldehyde 2aa

graphic file with name nihms-196262-f0007.jpg
Entry 1 (equiv) 2a (equiv) PAr3 (equiv) t [h] T [°C] Yieldb [%]
1 1.2 1 PPh3 (1) 36 0 0
2 1.2 1 PPh3 (1) 36 rtc 30
3 2.5 1 PPh3 (1) 36 rt 30
4 1.2 1 PPh3 (1) 36 40 37
5 1.2 1 PPh3 (1) 30 80 42
6 1.2 5 PPh3 (1) 30 80 29
7 1.2 1 PPh3 (5) 30 80 55
8 1.2 1 (4-FC6H4)3P (1) 144 rt 47
a

Allenic ester in CH3CN (5 mL) was added in one portion to a mixture of the other components in CH3CN (10 mL).

b

Isolated yield.

c

rt=room temperature.