Abstract
Bicyclic hydrazines, prepared by cycloaddition of cyclopentadiene
and diazo compounds, have great synthetic potential. Numerous asymmetric
transformations of these building blocks have been developed, involving
the electrophilicity of their strained double bond, ring-opening
reactions or skeletal rearrangements. All these transformations
are fully diastereoselective, and, in some cases, enantioselective,
enabling the preparation of a wide range of useful synthetic intermediates
from a single precursor in a few synthetic steps.
1 Introduction
2 Preparation and Conformational Properties of Bicyclic
3 Synthetic Transformations without Ring Fragmentation
3.1 Hydroboration
3.2 Hydroformylation and Halocarbomethoxylation
3.3 Dihydroxylation and Aminohydroxylation
3.4 Hydroarylation
3.5 Sequential Arylation-Alkynylation
3.6 Arylative Cyclization
3.7 Cyclopropanation
3.8 Pauson-Khand Reaction
3.9 Cycloaddition Reactions
4 Synthetic Transformations with Ring Fragmentation
4.1 Palladium-Catalyzed Ring-Opening Reactions
4.2 Copper-Catalyzed Ring-Opening Reactions
4.3 Rhodium-Catalyzed Ring-Opening Reactions
4.4 Ruthenium-Catalyzed Ring-Opening-Metathesis Reactions and
Oxidative Cleavage
5 Rearrangements
5.1 Rearrangements Involving Allylic Cations
5.2 Rearrangements Involving Aziridiniums
6 Synthetic Applications
7 Conclusion
Key words
asymmetric synthesis - bicyclic hydrazines - ring-opening reactions - amines - asymmetric catalysis
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