. Author manuscript; available in PMC: 2009 Aug 3.

Published in final edited form as: J Org Chem. 2008 Oct 21;73(22):8780–8784. doi: 10.1021/jo8015067

Table 4.

Chemoselectivity in Oxidatively Sensitive Ynamides.

entry	ynamides	α-keto-imides^a	yield [%]^b
1	43	50	46
2	44	51	35
3	45	52	15^c
4	46	53	40
5	47	54	65
6	48	55	39
7	49	56	88

4 equiv DMDO, acetone, it, 2.5 h.

Isolated yields.

Also isolated~33% yield of the epoxidized α-keto-imide.