Radical Cyclization Cascades of Unsaturated Meldrum’s Acid Derivatives

Brice Sautier; Sarah E. Lyons; Michael R. Webb; David J. Procter

doi:10.1021/ol2029367

Radical Cyclization Cascades of Unsaturated Meldrum’s Acid Derivatives

Brice Sautier, Sarah E. Lyons, Michael R. Webb, David J. Procter

Organic Chemistry Group

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

Abstract

Unsaturated, differentially substituted Meldrum's acid derivatives undergo cascade cyclizations upon ester reduction with SmI₂-H₂O. The cascade cyclizations proceed in good yield and with high diastereocontrol and convert simple, achiral starting materials to complex molecular architectures, bearing up to four stereocenters, in a single operation. The cascades are triggered by the generation and trapping of unusual radical-anions formed by electron transfer to the ester carbonyl.

Original language	English
Pages (from-to)	146-149
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	1
DOIs	https://doi.org/10.1021/ol2029367
Publication status	Published - 30 Nov 2011

Keywords

alcohols
cyclization
hydrocarbons
organic compounds
redox reactions

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10.1021/ol2029367

CCDC 849642: Experimental Crystal Structure Determination
Sautier, B. (Contributor), Lyons, S. E. (Contributor), Webb, M. R. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2012
DOI: 10.5517/ccxj3tb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccxj3tb&sid=DataCite
Dataset
CCDC 851256: Experimental Crystal Structure Determination
Sautier, B. (Contributor), Lyons, S. E. (Contributor), Webb, M. R. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2012
DOI: 10.5517/ccxksw3, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccxksw3&sid=DataCite
Dataset

Cite this

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title = "Radical Cyclization Cascades of Unsaturated Meldrum{\textquoteright}s Acid Derivatives",

abstract = "Unsaturated, differentially substituted Meldrum's acid derivatives undergo cascade cyclizations upon ester reduction with SmI2-H2O. The cascade cyclizations proceed in good yield and with high diastereocontrol and convert simple, achiral starting materials to complex molecular architectures, bearing up to four stereocenters, in a single operation. The cascades are triggered by the generation and trapping of unusual radical-anions formed by electron transfer to the ester carbonyl.",

keywords = "alcohols, cyclization, hydrocarbons, organic compounds, redox reactions",

author = "Brice Sautier and Lyons, {Sarah E.} and Webb, {Michael R.} and Procter, {David J.}",

year = "2011",

month = nov,

day = "30",

doi = "10.1021/ol2029367",

language = "English",

volume = "14",

pages = "146--149",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Radical Cyclization Cascades of Unsaturated Meldrum’s Acid Derivatives

AU - Sautier, Brice

AU - Lyons, Sarah E.

AU - Webb, Michael R.

AU - Procter, David J.

PY - 2011/11/30

Y1 - 2011/11/30

N2 - Unsaturated, differentially substituted Meldrum's acid derivatives undergo cascade cyclizations upon ester reduction with SmI2-H2O. The cascade cyclizations proceed in good yield and with high diastereocontrol and convert simple, achiral starting materials to complex molecular architectures, bearing up to four stereocenters, in a single operation. The cascades are triggered by the generation and trapping of unusual radical-anions formed by electron transfer to the ester carbonyl.

AB - Unsaturated, differentially substituted Meldrum's acid derivatives undergo cascade cyclizations upon ester reduction with SmI2-H2O. The cascade cyclizations proceed in good yield and with high diastereocontrol and convert simple, achiral starting materials to complex molecular architectures, bearing up to four stereocenters, in a single operation. The cascades are triggered by the generation and trapping of unusual radical-anions formed by electron transfer to the ester carbonyl.

KW - alcohols

KW - cyclization

KW - hydrocarbons

KW - organic compounds

KW - redox reactions

U2 - 10.1021/ol2029367

DO - 10.1021/ol2029367

M3 - Article

SN - 1523-7052

VL - 14

SP - 146

EP - 149

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

Radical Cyclization Cascades of Unsaturated Meldrum’s Acid Derivatives

Abstract

Keywords

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Datasets

CCDC 849642: Experimental Crystal Structure Determination

CCDC 851256: Experimental Crystal Structure Determination

Cite this