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The DA reaction is a very convenient method to synthesize six-carbon rings using conjugated dienes and olefins
.
However, the periselectivity, regioselectivity and stereoselectivity of the cross-DA reaction between two different conjugated dienes are poor, which limits its wide application in organic synthesis
The team used electron-deficient 2-pyrones and non-activated cyclic conjugated dienes as dienes, catalyzed by copper and chiral oxazoline ligands, to achieve a pericyclic selective asymmetric cross-DA reaction , Provides a new idea for the construction of functionalized chiral bicyclic structure, and based on this methodology, completed the high-efficiency asymmetric total synthesis of the biologically active molecules artemisinin and coronatine
.
Experiments and density functional theory calculations reveal a special "dual" reaction mode, that is, the reaction simultaneously obtains two kinds of [4+2] and [2+4] with the same enantioselectivity from a transition state.
Figure 1 Asymmetric cross Diels? Alder reaction
