Diastereoselective Syntheses of Spiro[indoline-3,4′-pyridin]-2-yl Carbamates via AgOTf/Ph3P‑Catalyzed Tandem Cyclizations of Tryptamine-Ynesulfonamides

Spiro­[indoline-3,4′-piperidine] is a significant structural scaffold in numerous polycyclic indole alkaloids with a variety of bioactivities. In this study, a synthetic strategy was developed to access spiro­[indoline-3,4′-pyridin]-2-yl carbamate via an AgOTf/PPh3-catalyzed tandem cyclization of tr...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-03, Vol.85 (5), p.3010-3019
Main Authors: Liang, Guoduan, Pang, Yadong, Ji, Yanjun, Zhuang, Kaitong, Li, Linji, Xie, Fukai, Yang, Lu, Cheng, Maosheng, Lin, Bin, Liu, Yongxiang
Format: Article
Language:English
Online Access:Get full text
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Summary:Spiro­[indoline-3,4′-piperidine] is a significant structural scaffold in numerous polycyclic indole alkaloids with a variety of bioactivities. In this study, a synthetic strategy was developed to access spiro­[indoline-3,4′-pyridin]-2-yl carbamate via an AgOTf/PPh3-catalyzed tandem cyclization of tryptamine-ynesulfonamides. The unique feature of this strategy is the efficient intermolecular capturing of the in situ generated spiroindoleninium intermediates with carbamates, leading to the diastereoselective syntheses of spiro­[indoline-3,4′-pyridin]-2-yl carbamate derivatives. A broad scope of this cyclization was demonstrated by a variety of tryptamine-ynesulfonamide substrates and several carbamates. A plausible mechanism of this reaction was proposed.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02839