Enantioselective Fluoroamination: 1,4-Addition to Conjugated Dienes Using Anionic Phase-Transfer Catalysis

Chiral‐anion phase‐transfer catalysis (PTC) has been applied towards the enantioselective fluorocyclization reactions of 1,3‐dienes. The method affords unprecedented fluorinated benz[f]isoquinoline and octahydroisoquinoline products in high yields and up to 96 % ee. New fluorinated amine reagents ou...

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Published inAngewandte Chemie (International ed.) Vol. 52; no. 30; pp. 7724 - 7727
Main Authors Shunatona, Hunter P., Früh, Natalja, Wang, Yi-Ming, Rauniyar, Vivek, Toste, F. Dean
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 22.07.2013
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
amination
Amines
asymmetric catalysis
Catalysis
Chemistry
Chemistry, Multidisciplinary
cyclization
Dienes
Fluorination
fluorine
phase-transfer catalysis
Physical Sciences
Science & Technology
Transformations
BROMOLACTONIZATION
1,3-DIENES
asymmetric catalysis
FLUORINATION
HALOGENATION
phase-transfer catalysis
cyclization
STRATEGIES
AFFINITY
CHEMISTRY
amination
DERIVATIVES
fluorine
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Summary:Chiral‐anion phase‐transfer catalysis (PTC) has been applied towards the enantioselective fluorocyclization reactions of 1,3‐dienes. The method affords unprecedented fluorinated benz[f]isoquinoline and octahydroisoquinoline products in high yields and up to 96 % ee. New fluorinated amine reagents outperformed Selectfluor in the desired transformation.
Bibliography:ark:/67375/WNG-Q0VDQ3NJ-X
We would like to thank the University of California at Berkeley for funding and David S. Tatum for X-ray crystallography analysis.
ArticleID:ANIE201302002
University of California at Berkeley
istex:B33632E0FB8D22D7E6302F13D5B71FF2753D997E
We would like to thank the University of California at Berkeley for funding and David S. Tatum for X‐ray crystallography analysis.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201302002