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. Author manuscript; available in PMC: 2010 Jan 29.
Published in final edited form as: Org Lett. 2009 Oct 1;11(19):4462. doi: 10.1021/ol901860b

Table 1.

A General Synthesis of 2-Amido-Furans.

entry ynamides 2-amido-furans yield [%]:a using Ab Bc
1 graphic file with name nihms170778t1.jpg graphic file with name nihms170778t2.jpg 18 82 44
2 graphic file with name nihms170778t3.jpg graphic file with name nihms170778t4.jpg 19 65 48
3 graphic file with name nihms170778t5.jpg graphic file with name nihms170778t6.jpg 20 77 48
4 graphic file with name nihms170778t7.jpg graphic file with name nihms170778t8.jpg 25 50 24
5 graphic file with name nihms170778t9.jpg graphic file with name nihms170778t10.jpg 26 47 29
6 graphic file with name nihms170778t11.jpg graphic file with name nihms170778t12.jpg 27a 49 32
7 27b 58 35
8 27c 61 47
9 graphic file with name nihms170778t13.jpg graphic file with name nihms170778t14.jpg 28 52 39
10 graphic file with name nihms170778t15.jpg graphic file with name nihms170778t16.jpg 30a 45d 37e
11 30b 24d 22e
a

Isolated yields.

b

When using A, all reactions were run in toluene at 80 °C with 2 mol % Rh2(OAc)4, and ynamide concn = 0.15 M. Reagent A [3.0 equiv] was delivered over 1–2 h as a solution in toluene [concn = 0.30 M] via a syringe pump.

c

When using B, all reactions were run in CH2Cl2 at rt for 1.5 h with 5 mol % Rh2(OAc)4 and 4Å MS, and ynamide concn = 0.15 M. Reagent B [2.0 equiv] was delivered as solid in 0.5 equiv portions over 1 h.

d

4.0 equiv of A and 5 mol % Rh2(OAc)4 were used, and temp was 110 °C.

e

Reactions were carried out in ClCH2CH2Cl [concn = 0.15 M] at 50 °C, and a total of 4.0 equiv of reagent B was used.