| Autor: |
Meyer CC; Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States., Verboom KL; Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States., Evarts MM; Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States., Jung WO; Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States., Krische MJ; Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States. |
| Abstrakt: |
The first systematic study of catalytic enantioselective 1,2-additions to acrolein is described. Specifically, using allyl alcohol as a tractable, inexpensive acrolein proelectrophile, iridium-catalyzed acrolein allylation is achieved with high levels of regio-, anti -diastereo-, and enantioselectivity. This process delivers 3-hydroxy-1,5-hexadienes, a useful compound class that is otherwise challenging to access via enantioselective catalysis. Two-fold use of this method unlocks concise total syntheses of amphidinolide R (9 vs 23 steps, LLS) and amphidinolide J (9 vs 23 or 26 steps, LLS), which are prepared in fewer than half the steps previously possible, and the first total synthesis of amphidinolide S (10 steps, LLS). |
