Abstract
Methyltin trichloride and indium(III) chloride promote ethyl pyruvate addition to cyclic allylic stannanes to produce α-methyl-α-hydroxy esters with excellent threo-diastereoselectivity (92-100% de). These reactions probably proceed via an initial γ-anti transmetallation followed by a metallo-ene cycloaddition involving internal chelation. The resulting esters can be diastereospecifically converted to the corresponding bicyclic bromolactones.
Original language | English |
---|---|
Pages (from-to) | 1640-1644 |
Number of pages | 5 |
Journal | Synthesis |
Volume | 1998 |
Issue number | 11 |
DOIs | |
Publication status | Published - Nov 1998 |
Externally published | Yes |