Enantioselective Organo-SOMO Cycloadditions: A Catalytic Approach to Complex Pyrrolidines from Olefins and Aldehydes

A new method to rapidly generate pyrrolidines via a SOMO-activated enantioselective (3 + 2) coupling of aldehydes and conjugated olefins has been accomplished. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting...

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Published inJournal of the American Chemical Society Vol. 134; no. 28; pp. 11400 - 11403
Main Authors Jui, Nathan T, Garber, Jeffrey A. O, Finelli, Fernanda Gadini, MacMillan, David W. C
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.07.2012
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Alkenes - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclization
Physical Sciences
Pyrrolidines - chemistry
Science & Technology
Stereoisomerism
CARBON BOND FORMATION
AZA-COPE REARRANGEMENTS
ACTIVATION
ONE-POT
STEREOCHEMISTRY
AZOMETHINE YLIDES
ORGANOCATALYSIS
AMINO ESTERS
DERIVATIVES
MOLECULES
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Summary:A new method to rapidly generate pyrrolidines via a SOMO-activated enantioselective (3 + 2) coupling of aldehydes and conjugated olefins has been accomplished. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnish a cationic intermediate which is vulnerable to nucleophilic addition of a tethered amine group. A range of olefins, including styrenes and dienes, are shown to provide stereochemically complex pyrrolidine products with high chemical efficiency and enantiocontrol.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja305076b