Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 10, Issue 10, Pages 2112-2116Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201500078
Keywords
aldol; amine; computation; organocatalysis; water
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Funding
- MEXT, Japan
- Grants-in-Aid for Scientific Research [26220803, 25109525, 26105733] Funding Source: KAKEN
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The origin of higher reactivity in water-accelerated asymmetric aldol reactions with our designed primary amine organocatalyst was elucidated by both computational and experimental methods. As suggested by the calculated transition-state structures for water-promoted imine-enamine isomerization, anti-selective aldol reaction and hemiaminal formation, the rate of this aldol reaction was found experimentally to be even more accelerated by the addition of cis-2-butene-1,4-diol as additive.
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