Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 12, Pages 2945-2949Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201605606
Keywords
aza-Diels-Alder; cyclic enones; cycloaddition; organocatalysis; regioselectivity; trienamine
Categories
Funding
- NSFC [21372160, 21125206, 21321061]
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Endo-type cross-conjugated trienamines between highly congested alpha'-alkylidene 2-cyclohexenones and a chiral primary amine catalyst serve as HOMO-raised dienophiles in inverse-electron-demand aza-Diels-Alder cycloadditions with a number of 1-azadiene substrates. The reactions exhibit exclusive beta, gamma-regioselectivity, and multifunctional products with high molecular complexity are efficiently constructed in excellent diastereo-and enantioselectivity (> 19: 1 d.r., up to 99% ee).
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