Indolylmethanols as C4 Synthons for the Asymmetric Synthesis of Indole-Fused Spiro Compounds
Tingting Zhang , Xiaochen Tian , Xin Shu , Honghan Li , Yihan Lu , Yang Wang
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (24) : 3483 -3488.
A novel asymmetric [4+2] cycloaddition of indolylmethanols with aurones via chiral phosphoric acid (CPA) catalysis has been established. Enantioenriched indole-fused spiro compounds were obtained in good yields (60%–89%) with excellent diastereoselectivities (up to >19 : 1 dr) and enantioselectivities (83%–99% ee) with broad substrate scope. This approach not only enabled the first catalytic asymmetric [4+2] cycloaddition of 3-methyl-2-indolylmethanols, but also represented different reactivity from traditional indolylmethanol chemistry. In this reaction, 3-methyl-2-indolylmethanols behaved as C4 synthons rather than C3 synthons.
Asymmetric catalysis / 3-Methyl-2-indolylmethanols / Aurones / [4+2] Cycloaddition / C4 synthons / Asymmetric synthesis / Chiral phosphoric acid / Indole-fused polycycles
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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