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. Author manuscript; available in PMC: 2008 Dec 20.
Published in final edited form as: Org Lett. 2007 Nov 29;9(26):5477–5480. doi: 10.1021/ol702401w

Table 3.

Carboamination of o-allyl vinyl amidesa

entry substrate product(s) yieldb(selectivity)
graphic file with name nihms63568t9.jpg graphic file with name nihms63568t10.jpg graphic file with name nihms63568t11.jpg
1 9a, R = H 10a, R = H 11a, R = H 72%(10a:11a = >20:1)
2 9b, R = OMe 10b, R = OMe 11b, R = OMe 74%(10b:11b = >20:1)
3 9c, R = Cl 10c, R = Cl 11c, R = Cl 71%(10c:11c = >20:1)
4c 9a, R = H 10a, R = H 11a, R = H 56%(10a:11a = 1.2:1)
5c graphic file with name nihms63568t12.jpg
12 		graphic file with name nihms63568t13.jpg
13 		38%
6c graphic file with name nihms63568t14.jpg
14 		graphic file with name nihms63568t15.jpg
15 		graphic file with name nihms63568t16.jpg
16 		49%(15:16 = 2.5:1)
a

Conditions. Substrate in DMF (0.1 M) was treated with Cu(EH)2 (3 equiv) and Cs2CO3 (1 equiv). The mixture was heated to 140 °C for 24 h in a pressure tube.

b

Yields refer to the sum of products isolated by chromatography on SiO2. The remainder of the material was either starting olefin or olefin-isomerized starting material.

c

Heated to 190 °C for 24 h.