A cation-directed two-component cascade approach to enantioenriched pyrroloindolines

Jamie R. Wolstenhulme; Alex Cavell; Matija Gredicak; Russell W. Driver; Martin D. Smith

doi:10.1039/c4cc06683a

A cation-directed two-component cascade approach to enantioenriched pyrroloindolines

Jamie R. Wolstenhulme
, Alex Cavell
, Matija Gredicak
, Russell W. Driver
, Martin D. Smith

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

21 Scopus citations

Abstract

A cascade approach to complex pyrroloindolines bearing all-carbon quaternary stereocentres has been developed. This two-component process uses a chiral ammonium salt to control diastereo- and enantioselectivity in the addition of isocyanides to functionalized alkenes to afford pyrroloindolines with up to three stereocentres. A mechanistic proposal involving intramolecular hydrogen bond activation of the isocyanide is described.

Original language	English
Pages (from-to)	13585-13588
Number of pages	4
Journal	Chemical Communications
Volume	50
Issue number	88
DOIs	https://doi.org/10.1039/c4cc06683a
State	Published - Nov 14 2014
Externally published	Yes

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AU - Driver, Russell W.

AU - Smith, Martin D.

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AB - A cascade approach to complex pyrroloindolines bearing all-carbon quaternary stereocentres has been developed. This two-component process uses a chiral ammonium salt to control diastereo- and enantioselectivity in the addition of isocyanides to functionalized alkenes to afford pyrroloindolines with up to three stereocentres. A mechanistic proposal involving intramolecular hydrogen bond activation of the isocyanide is described.

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A cation-directed two-component cascade approach to enantioenriched pyrroloindolines

Abstract

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