Conformational Effects in Diastereoselective Aryne Diels−Alder Reactions: Synthesis of Benzo-Fused [2.2.1] Heterobicycles

It was found that the diastereoselectivity of the Diels−Alder reaction between arynes and substituted furans is highly sensitive to substitution, which affects the reactive conformation. By varying the location of the groups on the diene partner, it is possible to obtain both excellent chemical yields and high stereoselectivity. This methodology offers rapid and convenient access to enantiomerically pure bicyclic scaffolds which are difficult to prepare by other means.

研究发现，芳基与取代呋喃之间的 Diels−Alder 反应的立体选择性对取代基的敏感性极高，这影响着反应的活性构象。通过调整双烯配体上基团的位置，可以实现优异的化学产率和高度的立体选择性。该方法为难以通过其他手段制备的对映异构体纯度高、双环骨架的快速便捷获取提供了可能。