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 in | Journal of the American Chemical Society Vol. 134; no. 28; pp. 11400 - 11403 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
18.07.2012
Amer Chemical Soc |
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| Online Access | Get full text |
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| Abstract | 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. |
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| AbstractList | 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. 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 furnishes 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. |
| Author | Jui, Nathan T Finelli, Fernanda Gadini Garber, Jeffrey A. O MacMillan, David W. C |
| AuthorAffiliation | Merck Center for Catalysis at Princeton University |
| AuthorAffiliation_xml | – name: Merck Center for Catalysis at Princeton University |
| Author_xml | – sequence: 1 givenname: Nathan T surname: Jui fullname: Jui, Nathan T – sequence: 2 givenname: Jeffrey A. O surname: Garber fullname: Garber, Jeffrey A. O – sequence: 3 givenname: Fernanda Gadini surname: Finelli fullname: Finelli, Fernanda Gadini – sequence: 4 givenname: David W. C surname: MacMillan fullname: MacMillan, David W. C email: dmacmill@princeton.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/22764834$$D View this record in MEDLINE/PubMed |
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| Copyright | Copyright © 2012 American Chemical Society |
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| Keywords | CARBON BOND FORMATION AZA-COPE REARRANGEMENTS ACTIVATION ONE-POT STEREOCHEMISTRY AZOMETHINE YLIDES ORGANOCATALYSIS AMINO ESTERS DERIVATIVES MOLECULES |
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| Snippet | A new method to rapidly generate pyrrolidines via a SOMO-activated enantioselective (3 + 2) coupling of aldehydes and conjugated olefins has been accomplished.... |
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| StartPage | 11400 |
| SubjectTerms | Aldehydes - chemistry Alkenes - chemistry Catalysis Chemistry Chemistry, Multidisciplinary Cyclization Physical Sciences Pyrrolidines - chemistry Science & Technology Stereoisomerism |
| Title | Enantioselective Organo-SOMO Cycloadditions: A Catalytic Approach to Complex Pyrrolidines from Olefins and Aldehydes |
| URI | http://dx.doi.org/10.1021/ja305076b http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000306457900027 https://www.ncbi.nlm.nih.gov/pubmed/22764834 https://search.proquest.com/docview/1027040946 https://pubmed.ncbi.nlm.nih.gov/PMC3408613 |
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