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. Author manuscript; available in PMC: 2012 Aug 31.
Published in final edited form as: J Am Chem Soc. 2011 Aug 3;133(34):13337–13348. doi: 10.1021/ja200231v

Table 5.

Phosphine-Catalyzed Annulations of the Azomethine Imine 1a with Ethyl 2,3-Butadienoate (2o)a

graphic file with name nihms316331u5.jpg
entry PR3 time (h) 3aob
yield (%)c
6b
yield (%)c
1 d 48 0 0
2 PPh3 24 8 19
3 EtPPh2 24 27 5
4 MePPh2 24 53 2
5 Me2PPh 24 69 15
6 PBu3 24 45 36
7 PMe3 12 62 3
8 HMPT 24 15 22
a

1.2 equiv of allenoate was used.

b

The structure of this compound was verified through single-crystal X-ray analysis.

c

Isolated yield.

d

Without phosphine catalyst.