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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 2.

Addition of Amines to α-Methyl Allenoatea

graphic file with name nihms-288843-t0005.jpg
entry R1 R2 yield (%)b 2 E:Zc
1 Ph p-Ts 94 2a 2.5:1
2 Bn p-Ts 94 2b 2.5:1
3 Boc p-Ts 83 2c 2:1
4 H p-Ts 53 2d 1:1.75
5 Ph Boc 0 2e N/A
6 phthalimide 71 2f E only
7 TsHN–NH2 57 2g 1.5:1
8 graphic file with name nihms-288843-t0006.jpg 92 2h 1:1.2
a

Reactions were performed using 1.1 equiv of the allenoate.

b

Isolated yield.

c

Determined through 1H NMR spectroscopic analysis.