Abstract
The reaction of the mono-anion of the bromoallyl sulfone 1 with aldehydes 2 was examined with the aim of obtaining selectively substituted tetrahydrofurans. At -100°C syn- and anti- open chain adducts 3 and 4 were isolated together with a low yield of 4-methylene-2,3-disubstituted tetrahydrofuran 5. In the presence of HMPA or at higher temperature the reaction led to formation of 2,5-dihydrofurans 6. The stereochemical results are consistent with initial addition of 1 to the aldehyde involving Li ion chelation.
| Original language | English |
|---|---|
| Pages (from-to) | 157-165 |
| Number of pages | 9 |
| Journal | Arkivoc |
| Volume | 2002 |
| Issue number | 8 |
| State | Published - 2002 |
Keywords
- Aldehydes
- Allyl sulfones
- Carbanaions
- Dihydrofurans
- Li chelation
- Michael additions