Bispidine, a bridged bicyclic diamine, has been widely utilized as a rigid scaffold in chiral chelating ligands in asymmetric synthesis. In particular, a chiral bispidine-quinolizidine hybrid, such as sparteine, was utilized in asymmetric synthesis involving a metal, exhibiting superior catalytic activity. In this study, we report the design and synthesis of a series of sparteine-derived organocatalysts and the utilization of these catalysts in tandem Michael addition–cyclization reactions. These catalysts have shown excellent catalytic reactivity and enantioselectivity, and the corresponding dihydropyrano[c]chromenes have been prepared in ≤99% yield and ≤99% ee with a low catalyst loading. The recycled catalysts maintain a good catalytic performance even after four cycles, and a gram-scale reaction with a 1% catalyst loading is also performed, providing the product in 96% yield and 98% ee.

中文翻译：

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金雀花硫脲：N手性双吡啶-喹啉西啶衍生有机催化剂的合成及其在二氢吡喃并[c]色烯不对称合成中的应用

Bispidine 是一种桥联双环二胺，已广泛用作不对称合成中手性螯合配体的刚性支架。特别是，手性双吡啶-喹啉西啶杂化物（例如金雀花碱）被用于涉及金属的不对称合成中，表现出优异的催化活性。在这项研究中，我们报告了一系列金雀花衍生的有机催化剂的设计和合成，以及这些催化剂在串联迈克尔加成环化反应中的应用。这些催化剂表现出优异的催化反应活性和对映选择性，并且以较低的催化剂负载量制备了相应的二氢吡喃并[ c ]色烯，收率≤99%，ee≤99%。回收的催化剂即使在经过四次循环后仍保持良好的催化性能，并且还进行了1%催化剂负载量的克级反应，提供了96%的收率和98%的ee的产物。