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 |
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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