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. 2014 Jul 3;16(13):3480-3.
doi: 10.1021/ol501409a. Epub 2014 Jun 25.

Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate

Thomas D Montgomery  1 , Antoinette E Nibbs, Ye Zhu, Viresh H Rawal
Affiliations

Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate

Thomas D Montgomery et al. Org Lett. .

Abstract

We report the intermolecular palladium-catalyzed reaction of tert-butyl propargyl carbonate with tryptamine derivatives or other indole-containing bis-nucleophiles. The reaction proceeds under mild conditions and with low catalyst loadings to afford novel spiroindolenine products in good to high yields.

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Figures

Scheme 1
Scheme 1. Pd-Catalyzed β-Functionalization of Indoles
Scheme 2
Scheme 2. Initial Experiments
Scheme 3
Scheme 3. Spirocyclization of Tryptamine Derivatives
Figure 1
Figure 1
Proposed catalytic cycle.
See this image and copyright information in PMC

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