Journal
TETRAHEDRON
Volume 67, Issue 17, Pages 3034-3040Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.03.007
Keywords
Organocatalysis; Cascade; Quinolizidine; Cyclization
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Funding
- National Natural Science Foundation of China [20802043, 21072125]
- Foundations of Education Commission of Shanghai Municipality [J50102]
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An organocatalyzed one-pot Michael addition-Pictet-Spengler sequence of beta-ketoamides and alpha,beta-unsaturated aldehydes was developed, which provided access to highly substituted indolo[2,3-alpha]quinolizidines and benzo[alpha]quinolizidines in moderate to good yields and good to excellent enantioselectivities. For aromatic alpha,beta-unsaturated aldehydes 1a-j products 10a-r containing a stable enol configuration were obtained. (C) 2011 Elsevier Ltd. All rights reserved.
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