Diastereodivergent synthesis of chromeno[2,3-b]chromenes by tuning all of the reactivity centers of isocyanoacetate†,10.1039/D2CC01632J

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Diastereodivergent synthesis of chromeno[2,3-b]chromenes by tuning all of the reactivity centers of isocyanoacetate†

Lei Wang,Zitong Huang,Xiaoyu Guo,Jian Liu,Jinhuan Dong,Xianxiu Xu

Chemical Communications Pub Date : 05/04/2022 00:00:00 , DOI:10.1039/D2CC01632J

Abstract

A novel diastereodivergent tricyclization of isocyanoacetates with o-quinone methides was accomplished for the efficient synthesis of chromeno[2,3-b]chromene derivatives. All three reactive centers of isocyanoacetate reacted sequentially with two o-QMs, affording the products with four adjacent stereocenters in a diastereoselective manner. The asymmetric version was preliminarily investigated.