Table 1.
Reactions of 2-(Phenylsulfonyl)-1,3-oxazole 1
| |||
|---|---|---|---|
| entry | electrophile | producta,b | yieldc (%) |
| 1 |
|
6
|
87 |
| 2 |
|
7
|
81 |
| 3 | n-Bu3SnCl |
8
|
86 |
| 4 | CH3I |
9
|
91 |
| 5 |
|
10
|
72 |
| 6 |
|
11
|
75 |
| 7 |
|
12
|
87 |
| 8 |
|
13
|
81 |
a
Reaction conditions: A THF solution of sulfone 1 (1.0 equiv; 2.0 mmol) was added into a solution of LDA (1.1 equiv) in THF at −78 °C. After stirring under N2 for 1 h, electrophile in THF solution was added with subsequent warming to 22 °C.
b
Products were purified by flash silica gel chromatography.
c
Yields are reported for isolated and purified product.