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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. [ABSTRACT FROM AUTHOR]

Aiming to develop efficient and general strategies for construction of complex and diverse polycyclic skeletons, we have successfully developed [4+3]IMPC (intramolecular parallel cycloaddition) of cyclopropane 1,1-diesters with [3]dendralenes. With a combination of the [4+3]IMPC and subsequent [4+ n] cycloadditions, trans-[5.3.0]decane skeleton and its corresponding structurally complex and diverse polycyclic variants could be constructed efficiently. This novel [4+3] cycloaddition reaction mode of donor-acceptor cyclopropanes proceeds as a result of the ring-strain relief of a trans-[3.3.0]octane. We strongly believe that the developed methods will demonstrate potential applications in natural products synthesis and drug discovery. [ABSTRACT FROM AUTHOR]

A novel Lewis acid‐catalyzed [3+2] intramolecular cross‐cycloaddition (IMCC) between aziridine 2,2‐diesters and conjugated dienes has been developed, which supplies a general and efficient strategy for construction of structurally complex and diverse aza‐[n.2.1] skeletons. The excellent structural diversity, the facile operation and the versatile post‐modifications will support the applications of the [3+2]IMCC in natural product synthesis and drug discovery. “Three begets all things of the world” comes from “Daodejing”, an immortal classic composed by Laozi, a great philosopher and thinker of ancient China. In this chemistry, the three‐membered aziridine means the “three” which begets the diversity and complexity by the IMCC strategy. For the full story see the Communication by Z. Wang et al. on page 17862 ff. [ABSTRACT FROM AUTHOR]