Skip to main content
. 2019 Mar 13;15:655–678. doi: 10.3762/bjoc.15.61

Table 6.

Preparation of oxazoles OX115 and 1,2-diketones DK113 through trifluoroacetic acid-promoted reaction of β-ketoenamides KE.a

entry KE R1 R2 R3 OX yield DK yield ref.

1 KE48 Bn n-Non Ph OX1 51% [45]
2 KE51 Bn t-Bu 2-Th DK1 83% [45]
3 KE52 Bn Ph CF3 OX2 74% [45]
4 KE53 Bn Ph Ph OX3 48% [45]
5 KE54 Bn Ph 2-Py OX4 64% [45]
6 KE56 PMB Ph CF3 OX5 53% [45]
7 KE57 2-THP cPr cPr OX6 51% DK2 <1% [45]
8 KE58 TMSE cPr cPr OX7 67% DK3 <1% [45]
9 KE60 TMSE t-Bu Me OX8 24% DK4 29% [45]
10 KE61 TMSE t-Bu CF3 OX9 61% DK5 31% [45]
11 KE62 TMSE t-Bu CH=CH2 DK6 73% [43]
12 KE63 TMSE t-Bu CH=CH-Me DK7 80% [43]
13 KE64 TMSE t-Bu CH=CH-Ph DK8 60% [43]
14 KE65 TMSE t-Bu CH=CH-C6H4-NO2 DK9 55% [43]
15 KE66 TMSE t-Bu CH=CH-2-Fu DK10 70% [43]
16 KE68 TMSE Ad cPr OX10 12% DK11 65% [45]
17 KE69 TMSE Ph CF3 OX11 98% -- -- [45]
18 KE70 TMSE Ph CH=CH-Me DK12 30%b [43]
19 KE71 TMSE Ph CH=CH-Ph DK13 33%b [43]
20 KE72 TMSE Ph C≡CH OX12 57% [45]
21 KE74 TMSE Ph 2-Py OX13 99% [45]
22 KE75 TMSE Ph 2-Th OX14 68% [45]
23 KE76 TMSE Ph Ac OX15 39% [45]

aAbbreviations: Ad = 1-adamantyl, Py = pyridyl, Fu = furyl, Th = thienyl, Ac = acetyl; all alkenyl substituents are E-configured. bIn addition, ca. 30% of a dimeric compound were isolated.