Diastereoselective Synthesis of Tetrabenzohydrofuran Spirooxindoles via Diethyl Phosphite-Mediated Coupling of Isatins with o‑Quinone Methides

Diethyl phosphite-initiated coupling of isatins with o-quinone methides (o-QMs) is reported. This reaction involves a cascade transformation initiated by base-promoted addition of phosphite to isatins, followed by [1,2]-phospha-Brook rearrangement. This generates α-phosphonyloxy enolates that are su...

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Published in:Journal of organic chemistry 2021-07, Vol.86 (13), p.8630-8640
Main Authors: Zhang, Xiyuan, Gao, Yanfeng, Liu, Yitong, Miao, Zhiwei
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creator Zhang, Xiyuan
Gao, Yanfeng
Liu, Yitong
Miao, Zhiwei
description Diethyl phosphite-initiated coupling of isatins with o-quinone methides (o-QMs) is reported. This reaction involves a cascade transformation initiated by base-promoted addition of phosphite to isatins, followed by [1,2]-phospha-Brook rearrangement. This generates α-phosphonyloxy enolates that are subsequently intercepted by o-QMs and finally intramolecular ring closure. This protocol was used to diastereoselectively synthesize a range of trans-tetrabenzohydrofuran spirooxindoles in moderate to good yields with moderate to excellent diastereoselectivities.
doi_str_mv 10.1021/acs.joc.1c00336
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title Diastereoselective Synthesis of Tetrabenzohydrofuran Spirooxindoles via Diethyl Phosphite-Mediated Coupling of Isatins with o‑Quinone Methides
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