Abstract
The development of practical methods to achieve catalytic enantioselective methods
for the transformation of C-H bonds is a research area of considerable current interest.
This review summarizes the recent developments in the rhodium-catalyzed intermolecular
C-H insertion chemistry of diazo compounds. The resulting rhodium carbenoid intermediates
are capable of spectacular chemoselectivity in the C-H transformations, as long as
the carbenoid is functionalized with both electron donor and acceptor groups. Examples
will be given to illustrate the synthetic scope of this chemistry and its application
in total synthesis. The reaction can be considered as a new strategic process for
synthesis. This will be illustrated by examples of reactions which compliment some
of the classic reactions of synthesis, such as the aldol reaction, the Mannich reaction,
the Claisen rearrangement and the Michael addition.
1 Introduction
2 C-H Activation of Alkanes
2.1 Benzylic C-H Activation
2.2 Allylic C-H Activation
2.3 C-H Activation α to Oxygen
2.4 C-H Activation α to Nitrogen
2.5 Kinetic Resolution and Double C-H Activation
3 Combined C-H Activation/Cope Rearrangement
4 C-H Activation Using Solid Supported Catalysts
5 Summary
Key words
rhodium carbenoid - enantioselective intermolecular C-H activation - C-H insertion
- aryldiazoacetates - chiral catalysis
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