Extending Pummerer reaction chemistry. Asymmetric synthesis of spirocyclic oxindoles via chiral indole-2-sulfoxides

Ken S. Feldman; Andrew G. Karatjas

doi:10.1021/ol0617244

Extending Pummerer reaction chemistry. Asymmetric synthesis of spirocyclic oxindoles via chiral indole-2-sulfoxides

Ken S. Feldman, Andrew G. Karatjas

Chemistry

Research output: Contribution to journal › Article › peer-review

59 Scopus citations

Abstract

The conversion of (S₈)-3-(ω-allylsilane and silyl enol ether)indole-2-sulfoxides to spirocyclic indolenines and then to oxindoles proceeds, in favorable cases, with moderate levels of chirality transfer from sulfur to C(3) of the indole core. A mechanistic model, which features either an Sn2′-like additive Pummerer sequence or a tight ion pair generated by an Sn1-like vinylogous Pummerer transform, is proposed to rationalize the sense of asymmetric induction.

Original language	English (US)
Pages (from-to)	4137-4140
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	18
DOIs	https://doi.org/10.1021/ol0617244
State	Published - Aug 31 2006

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0617244

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AU - Karatjas, Andrew G.

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N2 - The conversion of (S8)-3-(ω-allylsilane and silyl enol ether)indole-2-sulfoxides to spirocyclic indolenines and then to oxindoles proceeds, in favorable cases, with moderate levels of chirality transfer from sulfur to C(3) of the indole core. A mechanistic model, which features either an Sn2′-like additive Pummerer sequence or a tight ion pair generated by an Sn1-like vinylogous Pummerer transform, is proposed to rationalize the sense of asymmetric induction.

AB - The conversion of (S8)-3-(ω-allylsilane and silyl enol ether)indole-2-sulfoxides to spirocyclic indolenines and then to oxindoles proceeds, in favorable cases, with moderate levels of chirality transfer from sulfur to C(3) of the indole core. A mechanistic model, which features either an Sn2′-like additive Pummerer sequence or a tight ion pair generated by an Sn1-like vinylogous Pummerer transform, is proposed to rationalize the sense of asymmetric induction.

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Extending Pummerer reaction chemistry. Asymmetric synthesis of spirocyclic oxindoles via chiral indole-2-sulfoxides

Abstract

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