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Lewis Acid‐Catalyzed Intramolecular [3+2] Cross‐Cycloaddition of Aziridine 2,2‐Diesters with Conjugated Dienes for Construction of Aza‐[ n .2.1] Skeletons
Author(s) -
Zhan Yizhou,
Liu Tao,
Ren Jun,
Wang Zhongwen
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704695
Subject(s) - intramolecular force , aziridine , conjugated system , cycloaddition , chemistry , lewis acids and bases , catalysis , combinatorial chemistry , organic chemistry , ring (chemistry) , polymer
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.