Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 71, Pages 17862-17866Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201704695
Keywords
aziridine; bridged ring; cycloaddition; medium-sized ring; regioselectivity
Categories
Funding
- NSFC [21372126, 21572103, 21421062]
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A novel Lewis acid-catalyzed [3+2] intramolecular cross-cycloaddition (IMCC) between aziridine 2,2-diesters and conjugated dienes has been developed. This is the first regiospecific IMCC of intramolecular 1,3-dipolar cycloadditions of azomethine ylides with carbon=carbon double bonds, and supplies a general and efficient strategy for construction of structurally complex and diverse aza-[n.2.1] skeletons. The [3+2]IMCC could be carried out under mild conditions and in gram scale. More importantly, 3-alkyl-substituted aziridines were also successful. The excellent structural diversity, the facile operation and the versatile post-modifications will support the applications of the [3+2]IMCC in natural products synthesis and drugs discovery.
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