Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 8, Pages 3443-3448Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404550
Keywords
[3+3] cycloaddition; aminocatalysis; cascade catalysis; enantioselectivity; regioselectivity
Categories
Funding
- NSFC [21122056, 21372160, 21321061]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT13031]
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An asymmetric formal [3+3] cycloaddition process with diversely structured aliphatic ketones and electron-deficient cyclic 1-azadienes was developed by cascade enamine-enamine catalysis of a cinchona-based primary amine. This sequence involved a domino Michael addition-Mannich reaction to afford spirocyclic architectures in excellent diastereo- and enantioselectivity. Importantly, high regioselectivity was realized for a number of unsymmetrical aliphatic ketone substrates.
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