| Abstract
| - Optically active (1S,3R,4R)-3-[N-(trans-2,5-dialkyl)pyrrolidinyl]methyl-2-azabicyclo-[2.2.1]heptaneswere evaluated as catalysts for the enantioselective β-elimination of meso-epoxides. The (2R,5R)-dimethylpyrrolidinyl-substituted catalyst 4 exhibited exceptionally high enantioselectivity andreactivity, and several substrates were rearranged with enantioselectivities of 98−99% ee. Inaddition, the use of 4 allowed the first successful, true catalytic rearrangement of the difficultsubstrates cyclopentene oxide (81%, 96% ee) and (Z)-4-octene oxide (80%, 91% ee).
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