Detour and direct induction of methyl-containing chiral centers via catalytic C-H or C-C bond formation

Kohei Endo, Takanori Shibata

Research output: Contribution to journalReview article

10 Citations (Scopus)

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 S′ 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 S′ Methylation 3.3 Conjugate Addition 3.4 Ring-Opening Reaction 3.5 Trifluoromethylation 4 Concluding Remarks.

Original languageEnglish
Pages (from-to)1427-1452
Number of pages26
JournalSynthesis
Volume44
Issue number10
DOIs
Publication statusPublished - 2012 Apr 18

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Keywords

  • asymmetric catalysis
  • asymmetric synthesis
  • chirality
  • methylation
  • natural products

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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