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Synthesis 1991; 1991(9): 665-680
DOI: 10.1055/s-1991-26541
review
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Catalytic Asymmetric Hydrogen Migration of Allylamines

Sei Otsuka* , Kazuhide Tani
  • *Otsuka Pharmaceutical Co. Ltd., 771-01 Tokushima, Japan
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Publication Date:
29 April 2002 (online)

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This review describes some preparative aspects and practical applications of BINAP-Rh(I) catalyzed enantioselective isomerization of prochiral allylamines recently developed through the joint effort of several groups in Japan. In addition, the novel, sophisticated reaction mechanisms are discussed. 1. Introduction 2. Catalyst Development 2.1. Cobalt Catalysts 2.2. Rhodium Catalysts 2.3. The Ligand BINAP 3. Preparative Aspects 3.1. Isomerization on a Laboratory Scale 3.2. The Industrial Process 4. Substrates and the Scope 4.1. Allylamine 4.2. Allyl Alcohol 5. Reaction Mechanisms 5.1. Catalytic Pathways 5.2. Mechanism of Chiral Recognition 5.3. Conclusion 6. Applications 6.1. (-)-Menthol 6.2. Citronellol 6.3. Citronellal Derivatives 6.4. α-Tocopherol Side Chain 6.5. Methoprene

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