FeCl3-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis

Exploiting catalytic carbonyl–olefin metathesis is an ongoing challenge in organic synthesis. Reported herein is an FeCl3‐catalyzed ring‐closing carbonyl–olefin metathesis. The protocol allows access to a range of carbo‐/heterocyclic alkenes with good efficiency and excellent trans diastereoselectiv...

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Published inAngewandte Chemie (International ed.) Vol. 55; no. 35; pp. 10410 - 10413
Main Authors Ma, Lina, Li, Wenjuan, Xi, Hui, Bai, Xiaohui, Ma, Enlu, Yan, Xiaoyu, Li, Zhiping
Format Journal Article
LanguageEnglish
Published WEINHEIM Blackwell Publishing Ltd 22.08.2016
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alkenes
carbocycles
Carbonyls
Catalysis
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Decomposition reactions
Efficiency
heterocycles
iron
Metathesis
Physical Sciences
Science & Technology
ALKYLIDENE
ORGANIC-SYNTHESIS
KETONES
carbocycles
metathesis
heterocycles
iron
alkenes
PHOTOPROTOLYTIC OXAMETATHESIS
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Summary:Exploiting catalytic carbonyl–olefin metathesis is an ongoing challenge in organic synthesis. Reported herein is an FeCl3‐catalyzed ring‐closing carbonyl–olefin metathesis. The protocol allows access to a range of carbo‐/heterocyclic alkenes with good efficiency and excellent trans diastereoselectivity. The methodology presents one of the rare examples of catalytic ring‐closing carbonyl–olefin metathesis. This process is proposed to take place by FeCl3‐catalyzed oxetane formation followed by retro‐ring‐opening to deliver metathesis products. Ironing it out: The title reaction allows access to a range of carbo‐/heterocyclic alkenes. The reaction is proposed to take place by FeCl3‐catalyzed oxetane formation followed by retro‐ring‐opening to deliver the metathesis products.
Bibliography:ark:/67375/WNG-J39FZ9X5-8
ArticleID:ANIE201604349
National Science Foundation of China - No. 21272267
istex:33FC062FE16B7A3AAB6F0B1B3BE3693ABD35EF14
These authors contributed equally to this work.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201604349