Samarium Diiodide Catalyzed Radical Cascade Cyclizations that Construct Quaternary Stereocenters

Huan Ming Huang; Qiong He; David J. Procter

doi:10.1055/s-0039-1690196

Samarium Diiodide Catalyzed Radical Cascade Cyclizations that Construct Quaternary Stereocenters

Huan Ming Huang, Qiong He, David J. Procter^*

^*Corresponding author for this work

Organic Chemistry Group

UMIST

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

Abstract

SmI ₂ -catalyzed radical cascade cyclizations were used to generate complex carbocyclic products bearing quaternary stereocenters with high selectivity. Bicyclic scaffolds containing four contiguous stereocenters and one quaternary stereocenter were obtained in excellent yields (up to 99%) and with high diastereocontrol by using 5 mol% of SmI ₂ at ambient temperature in the absence of co-reductants or additives. Mechanistic studies support a radical relay mechanism.

Original language	English
Pages (from-to)	45-50
Number of pages	6
Journal	SYNLETT
Volume	31
Issue number	1
DOIs	https://doi.org/10.1055/s-0039-1690196
Publication status	Published - 2020

Keywords

cascade reaction
catalysis
cyclization
radical relay
samarium diiodide

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10.1055/s-0039-1690196

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title = "Samarium Diiodide Catalyzed Radical Cascade Cyclizations that Construct Quaternary Stereocenters",

abstract = "SmI 2 -catalyzed radical cascade cyclizations were used to generate complex carbocyclic products bearing quaternary stereocenters with high selectivity. Bicyclic scaffolds containing four contiguous stereocenters and one quaternary stereocenter were obtained in excellent yields (up to 99%) and with high diastereocontrol by using 5 mol% of SmI 2 at ambient temperature in the absence of co-reductants or additives. Mechanistic studies support a radical relay mechanism.",

keywords = "cascade reaction, catalysis, cyclization, radical relay, samarium diiodide",

author = "Huang, {Huan Ming} and Qiong He and Procter, {David J.}",

year = "2020",

doi = "10.1055/s-0039-1690196",

language = "English",

volume = "31",

pages = "45--50",

journal = "SYNLETT",

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T1 - Samarium Diiodide Catalyzed Radical Cascade Cyclizations that Construct Quaternary Stereocenters

AU - Huang, Huan Ming

AU - He, Qiong

AU - Procter, David J.

PY - 2020

Y1 - 2020

N2 - SmI 2 -catalyzed radical cascade cyclizations were used to generate complex carbocyclic products bearing quaternary stereocenters with high selectivity. Bicyclic scaffolds containing four contiguous stereocenters and one quaternary stereocenter were obtained in excellent yields (up to 99%) and with high diastereocontrol by using 5 mol% of SmI 2 at ambient temperature in the absence of co-reductants or additives. Mechanistic studies support a radical relay mechanism.

AB - SmI 2 -catalyzed radical cascade cyclizations were used to generate complex carbocyclic products bearing quaternary stereocenters with high selectivity. Bicyclic scaffolds containing four contiguous stereocenters and one quaternary stereocenter were obtained in excellent yields (up to 99%) and with high diastereocontrol by using 5 mol% of SmI 2 at ambient temperature in the absence of co-reductants or additives. Mechanistic studies support a radical relay mechanism.

KW - cascade reaction

KW - catalysis

KW - cyclization

KW - radical relay

KW - samarium diiodide

UR - http://www.scopus.com/inward/record.url?scp=85076883980&partnerID=8YFLogxK

U2 - 10.1055/s-0039-1690196

DO - 10.1055/s-0039-1690196

M3 - Article

AN - SCOPUS:85076883980

SN - 0936-5214

VL - 31

SP - 45

EP - 50

JO - SYNLETT

JF - SYNLETT

IS - 1

ER -

Samarium Diiodide Catalyzed Radical Cascade Cyclizations that Construct Quaternary Stereocenters

Abstract

Keywords

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Samarium Diiodide Catalyzed Radical Cascade Cyclizations that Construct Quaternary Stereocenters

Abstract

Keywords

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Equipment

EPSRC National Research Facility for Electron Paramagnetic Resonance

Cite this