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Synthesis 2018; 50(15): 2799-2823
DOI: 10.1055/s-0037-1610143
DOI: 10.1055/s-0037-1610143
review
Norbornene in Organic Synthesis
Financial support from the ‘973’ Program (2015CB856500) and the NSFC (Grant No. 21672159) is gratefully acknowledged.Further Information
Publication History
Received: 24 February 2018
Accepted after revision: 21 March 2018
Publication Date:
25 June 2018 (online)
Dedicated to Prof. Kang Zhao on the occasion of his 60th birthday
Abstract
The norbornene skeleton possesses an alkene functionality with a fixed conformation, and represents unique reactivity. The use of norbornene and analogues as substrates is overviewed; reactivities are discussed as well as the role of norbornenes as ligands assisting modern organic transformations.
1 Introduction
2 Synthesis of Substituted Norbornenes
2.1 Preparation of Functionalized Norbornenes by Deprotonation and Substitution Reactions
2.2 Preparation of Functionalized Norbornenes under Palladium-Catalyzed Reaction Conditions
2.3 Alkylation of Norbornene
2.4 Multistep Synthesis
3 Synthesis of Substituted Norbornanes
3.1 Three-Membered-Ring Formation
3.2 Formation of Four-Membered Rings
3.3 Five- and Six-Membered Ring Formation
3.4 Syntheses of Difunctionalized Norbornanes
4 Synthesis of Cyclopentanes
4.1 Oxidation Reactions
4.2 Ring-Opening Cross Metathesis (ROCM)
4.3 Ring-Opening Metathesis Polymerization (ROMP)
4.4 Palladium-Catalyzed Ring-Opening of Norbornene
5 Norbornene-Mediated Reactions
5.1 Palladium Insertion into Carbon–Halide Bonds
5.2 Palladium Insertion into N–H and C–H Bonds
5.3 Norbornene as Ligand in Mediated Reactions
6 Conclusion
-
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