Palladium(II) Catalyzed C–H Functionalization Cascades for the Diastereoselective Synthesis of Polyheterocycles

Michael Watt; Kevin Booker-Milburn

doi:10.1021/acs.orglett.6b02947

Palladium(II) Catalyzed C–H Functionalization Cascades for the Diastereoselective Synthesis of Polyheterocycles

Michael Watt, Kevin Booker-Milburn

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Abstract

C−H activation offers huge potential in the generation of complex structures from simple starting materials. Herein we report the development of a highly diastereoselective palladium(II) catalyzed C−H functionalization cascade to produce novel, unsaturated polyheterocycles from simple diene-tethered heterocyclic starting materials. The reaction is applicable to both indole and pyrrole based substrates and tolerates a wide range of functional group substitutions around the heteroaromatic core. The polyheterocyclic products are formed as single diastereoisomers, with two new stereocenters formed in a single step.

Original language	English
Pages (from-to)	5716-5719
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.6b02947
Publication status	Published - 27 Oct 2016

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Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
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title = "Palladium(II) Catalyzed C–H Functionalization Cascades for the Diastereoselective Synthesis of Polyheterocycles",

abstract = "C−H activation offers huge potential in the generation of complex structures from simple starting materials. Herein we report the development of a highly diastereoselective palladium(II) catalyzed C−H functionalization cascade to produce novel, unsaturated polyheterocycles from simple diene-tethered heterocyclic starting materials. The reaction is applicable to both indole and pyrrole based substrates and tolerates a wide range of functional group substitutions around the heteroaromatic core. The polyheterocyclic products are formed as single diastereoisomers, with two new stereocenters formed in a single step.",

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N2 - C−H activation offers huge potential in the generation of complex structures from simple starting materials. Herein we report the development of a highly diastereoselective palladium(II) catalyzed C−H functionalization cascade to produce novel, unsaturated polyheterocycles from simple diene-tethered heterocyclic starting materials. The reaction is applicable to both indole and pyrrole based substrates and tolerates a wide range of functional group substitutions around the heteroaromatic core. The polyheterocyclic products are formed as single diastereoisomers, with two new stereocenters formed in a single step.

AB - C−H activation offers huge potential in the generation of complex structures from simple starting materials. Herein we report the development of a highly diastereoselective palladium(II) catalyzed C−H functionalization cascade to produce novel, unsaturated polyheterocycles from simple diene-tethered heterocyclic starting materials. The reaction is applicable to both indole and pyrrole based substrates and tolerates a wide range of functional group substitutions around the heteroaromatic core. The polyheterocyclic products are formed as single diastereoisomers, with two new stereocenters formed in a single step.

U2 - 10.1021/acs.orglett.6b02947

DO - 10.1021/acs.orglett.6b02947

M3 - Article (Academic Journal)

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JO - Organic Letters

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ER -

Palladium(II) Catalyzed C–H Functionalization Cascades for the Diastereoselective Synthesis of Polyheterocycles

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