Stereocontrolled Construction of Spirooxindole-Containing 5,6,7,8-Tetrahydropyrrolo[1,2‑a]pyridine via Michael/Friedel–Crafts Domino Reaction Promoted by Secondary Amine-Squaramide

Stereocontrolled Construction of Spirooxindole-Containing 5,6,7,8-Tetrahydropyrrolo[1,2‑a]pyridine via Michael/Friedel–Crafts Domino Reaction Promoted by Secondary Amine-Squaramide

An asymmetric Michael/Friedel–Crafts cascade reaction with Morita–Baylis–Hillman (MBH) nitroallylic esters and 3-pyrrolyloxindoles has been developed for the stereoselective construction of spirooxindole-containing tetrahydroindolizines. A range of tetracyclic scaffolds possessing three consecutive...

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Veröffentlicht in:Organic letters 2024-03, Vol.26 (11), p.2152-2157
Hauptverfasser: Yin, Pengxuan, Zhou, Zijie, Shi, Lingsheng, Xiang, Chengzhi, Ye, Ling, Han, Min, Shi, Zhichuan, Zhao, Zhigang, Li, Xuefeng
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container_end_page 2157
container_issue 11
container_start_page 2152
container_title Organic letters
container_volume 26
creator Yin, Pengxuan
Zhou, Zijie
Shi, Lingsheng
Xiang, Chengzhi
Ye, Ling
Han, Min
Shi, Zhichuan
Zhao, Zhigang
Li, Xuefeng
description An asymmetric Michael/Friedel–Crafts cascade reaction with Morita–Baylis–Hillman (MBH) nitroallylic esters and 3-pyrrolyloxindoles has been developed for the stereoselective construction of spirooxindole-containing tetrahydroindolizines. A range of tetracyclic scaffolds possessing three consecutive chiral centers, including an all-carbon quaternary stereocenter, were generated in 53–85% isolated yields with high diastereoselectivities and enantiopurities (≥3:1 dr, 50–98% ee). A newly synthesized bifunctional secondary amine/squaramide organocatalyst was demonstrated to exhibit better stereochemical control than their tertiary analogues.
doi_str_mv 10.1021/acs.orglett.4c00073
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title Stereocontrolled Construction of Spirooxindole-Containing 5,6,7,8-Tetrahydropyrrolo[1,2‑a]pyridine via Michael/Friedel–Crafts Domino Reaction Promoted by Secondary Amine-Squaramide
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