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Synthesis 2012; 44(10): 1427-1452
DOI: 10.1055/s-0031-1290869
DOI: 10.1055/s-0031-1290869
review
Detour and Direct Induction of Methyl-Containing Chiral Centers via Catalytic C–H or C–C Bond Formation
Further Information
Publication History
Received: 31 January 2012
Accepted after revision: 24 February 2012
Publication Date:
17 April 2012 (online)
Abstract
The asymmetric induction of chiral centers bearing a methyl group is a fundamental protocol for the synthesis of valuable molecules in biologically active compounds. However, the direct asymmetric methylation is typically difficult to achieve. The present review describes recent representatives of detour and direct approaches to the construction of methyl-containing chiral centers via catalytic C–H or C–C bond formation.
1 Introduction
2 Detour Approaches
2.1 Enzymatic Transformation
2.2 Hydrogenation (Reduction)
2.3 Hydroboration and Suzuki–Miyaura Cross-Coupling
2.4 Hydroformylation
2.5 Cross-Coupling Reaction
2.6 Conjugate Addition
2.7 SN2′ Methylation
2.8 α-Alkylation
2.9 C–H Functionalization
2.10 Friedel–Crafts Reaction
2.11 Diels–Alder Reaction
2.12 Miscellaneous
3 Direct Approaches
3.1 Carbometallation
3.2 SN2′ Methylation
3.3 Conjugate Addition
3.4 Ring-Opening Reaction
3.5 Trifluoromethylation
4 Concluding Remarks
-
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