Synergistic Catalysis: Metal/Proton-Catalyzed Cyclization of Alkynones Toward Bicyclo[3.n.1]alkanones
A highly efficient and practical synergistically metal/proton‐catalyzed Conia–ene reaction for the synthesis of bicyclo[3.n.1]alkanones has been developed. This synergistic catalysis was successfully utilized in modifying natural compounds such as methyl dihydrojasmonate, α,β‐thujone, and 5α‐cholest...
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Published in | Angewandte Chemie (International ed.) Vol. 54; no. 32; pp. 9414 - 9418 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
03.08.2015
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
Edition | International ed. in English |
Subjects | |
Online Access | Get full text |
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Summary: | A highly efficient and practical synergistically metal/proton‐catalyzed Conia–ene reaction for the synthesis of bicyclo[3.n.1]alkanones has been developed. This synergistic catalysis was successfully utilized in modifying natural compounds such as methyl dihydrojasmonate, α,β‐thujone, and 5α‐cholestan‐3‐one. Furthermore, the bridged carbonyl group of bicyclo[3.2.1]alkanones could be easily attacked by nucleophiles to give the ring‐opened cycloheptenone products or bicyclo[4.2.1]amide in excellent yields. These reactions provide rapid access to a diverse range of cyclic structures from simple starting materials or naturally occurring compounds.
A highly efficient and practical synergistically metal/proton‐catalyzed Conia–ene reaction for the synthesis of bicyclo[3.n.1]alkanones has been developed. The reaction was successfully utilized in modifying natural compounds such as methyl dihydrojasmonate, α,β‐thujone, and 5α‐cholestan‐3‐one. Furthermore, the bicyclo[3.2.1]alkanones can be ring‐opened by nucleophiles to give the corresponding products in excellent yields. |
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Bibliography: | National Basic Research Program of China - No. 2011CB808600 Guangdong Natural Science Foundation - No. 2014A030313229; No. 10351064101000000 ark:/67375/WNG-0FJVWT6P-P istex:8F24B52AB96AA59AE2C4B84D06EA0F5FB8B7FAB4 ArticleID:ANIE201504964 This work was supported by the National Basic Research Program of China (973 Program) (2011CB808600), the National Natural Science Foundation of China (21172077, 21372086, and 21422204), Guangdong Natural Science Foundation (2014A030313229 and 10351064101000000), SRF for ROCS, State Education Ministry, and the Fundamental Research Funds for the Central Universities, SCUT. National Natural Science Foundation of China - No. 21172077; No. 21372086; No. 21422204 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1433-7851 1521-3773 |
DOI: | 10.1002/anie.201504964 |