Gold-Catalyzed Diastereoselective Formal Intermolecular [4 + 2 + 1] Cycloaddition of 1,3-Dien-8-yne with Diazo Ester
Yu-Jiang Wang1, Xiao-Xiao Li2, Zili Chen1
1Department of Chemistry, Renmin University of China, Beijing 100872, China.
Abstract:
The first example of gold-catalyzed formal intermolecular [4 + 2 + 1] cycloaddition was developed using 1,3-dien-8-yne as C4 and C2 units and diazo ester as the C1 unit, which provides expedient access to a series of structurally complicated [5.3.0] bicyclic adducts in moderate yields with moderate to high diastereoselectivities. The key route involved a cascade process of dienyne cycloisomerization, cyclopropyl gold carbene's trapping, and subsequent divinyl cyclopropane (DVCP) Cope rearrangement.
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