Control elements operative in the β-hydroxy ester dianionic Claisen rearrangements are probed. Stereochemistry at Cβ dictates face selectivity at Cα and Cβ′ in 1 → 2-5, but only to the extent that it controls ester enolate geometry since a second important control element, chair/boat selectivity, is also operative. Evidence for excellent (E)-enolate selectivity in the enolization of β-hydroxy esters (cf. 7 and 13) and substrate-dependent chair/boat selectivity in the ensuing Claisen rearrangement are described.
|Original language||English (US)|
|Number of pages||4|
|Journal||Journal of Organic Chemistry|
|State||Published - 1988|
ASJC Scopus subject areas
- Organic Chemistry