Abstract
The deprotonation and the tin-lithium exchange of the glycosylstannane 1 are not decoupled when BuLi is used. Deuteration experiments show that the side product 2H (glycitol) is formed during the deprotonation/transmetallation reaction sequence and not by subsequent protonation of the glycosyl dianion. Decoupling of the two reaction steps is possible by using MeLi*LiBr for deprotonation and BuLi for tin lithium exchange. The described procedure optimizes the preparation of a β-lithium-configurated glycosyl dianion by preventing the reduction side reaction.
| Original language | English |
|---|---|
| Pages (from-to) | 1903-1906 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 38 |
| Issue number | 11 |
| DOIs | |
| State | Published - 17 Mar 1997 |