Abstract
Unmodified aldehydes add in 1,4-manner to electron deficient olefins in the presence of a catalytic amount of diethylaminotrimethylsilane. Reaction with methyl α- haloacrylates provided formylcyclopropanecarboxylates by domino conjugate addition-alkylation. Aldol condensation afforded unsaturated aldehydes. The reaction was revealed to proceed via catalytic enamine pathway. Total syntheses of several bisabolane type sesquiterpenoids have been accomplished according to this protocol.
Keywords: diethylaminotrimethylsilane, conjugate addition, cyclopropanation, aldol condensation
Mini-Reviews in Organic Chemistry
Title: Highly Efficient and Environmentally Benign Catalytic Enamine Reaction of Unmodified Aldehydes and its Application to Terpenoid Syntheses
Volume: 1 Issue: 2
Author(s): Hisahiro Hagiwara
Affiliation:
Keywords: diethylaminotrimethylsilane, conjugate addition, cyclopropanation, aldol condensation
Abstract: Unmodified aldehydes add in 1,4-manner to electron deficient olefins in the presence of a catalytic amount of diethylaminotrimethylsilane. Reaction with methyl α- haloacrylates provided formylcyclopropanecarboxylates by domino conjugate addition-alkylation. Aldol condensation afforded unsaturated aldehydes. The reaction was revealed to proceed via catalytic enamine pathway. Total syntheses of several bisabolane type sesquiterpenoids have been accomplished according to this protocol.
Export Options
About this article
Cite this article as:
Hagiwara Hisahiro, Highly Efficient and Environmentally Benign Catalytic Enamine Reaction of Unmodified Aldehydes and its Application to Terpenoid Syntheses, Mini-Reviews in Organic Chemistry 2004; 1 (2) . https://dx.doi.org/10.2174/1570193043488881
DOI https://dx.doi.org/10.2174/1570193043488881 |
Print ISSN 1570-193X |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6298 |
Call for Papers in Thematic Issues
Active Alkaloids: Structure, Mechanism of Action, Chemical Synthesis, and Biosynthesis
The scope of this topic encompasses the structure, mechanism of action, chemical synthesis, and biosynthesis of active alkaloids. Alkaloids, a class of nitrogen-containing organic compounds with alkaline properties, originate from a diverse array of sources. Many alkaloids exhibit significant biological activities and serve as key constituents in numerous medicinal plants. ...read more
Advancement in Petroleum Geochemistry
The scope of the thematic issue on advancements in petroleum geochemistry encompasses a broad range of cutting-edge research and technological innovations. This issue aims to highlight the latest developments in understanding the chemical and physical properties of petroleum and its geological formations. Key areas of focus include: Unconventional Resources: Exploring ...read more
Advancements in Synthesis of Bioactive Compounds
This thematic issue focuses on elucidating advanced synthetic strategies for bioactive compounds, with the primary objective of deepening understanding of the rational design and construction of target molecules. The exploration encompasses a diverse range of techniques, established name reactions, and cutting-edge synthetic methodologies. Specifically, the issue delves into the synthesis ...read more
Advances in Sustainable Synthesis and Applications of Cyclic Carbonates: From Green Chemistry to Advanced Materials
Cyclic carbonates have become a focus of attention because of their potential in sustainable chemistry, energy solutions, and advanced materials. Recent breakthroughs in their synthesis emphasize the use of CO₂ as a renewable feedstock, which is a step toward reducing carbon emissions. New catalytic processes, including both traditional metal catalysts ...read more
Related Journals
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers