Catalytic Asymmetric Hydrogen Migration of Allylamines
- 1 January 1991
- journal article
- review article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1991 (09) , 665-680
- https://doi.org/10.1055/s-1991-26541
Abstract
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. MethopreneKeywords
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