Synthesis and Applications of Binaphthylic C2-Symmetry Derivatives as Chiral Auxiliaries in Enantioselective Reactions

Carlo Rosini; Livia Franzini; Andrea Raffaelli; Piero Salvadori

doi:10.1055/s-1992-26147

Synthesis 1992; 1992(6): 503-517
DOI: 10.1055/s-1992-26147

review

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Synthesis and Applications of Binaphthylic C₂-Symmetry Derivatives as Chiral Auxiliaries in Enantioselective Reactions

Carlo Rosini^* , Livia Franzini, Andrea Raffaelli, Piero Salvadori

^*Centro CNR Macromolecole Stereordinate ed Otticamente Attive, Dipartimento di Chimica e Chimica Industriale, Universitá di Pisa, Via Risorgimento 35, I-56126 Pisa, Italy

Abstract

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In this review, after a general introduction devoted to show the importance of the role played by C ₂-symmetry chiral auxiliaries to provide high levels of stereoselection, a complete survey of the preparation and use of optically active 1,1′-binaphthyl derivatives as chiral auxiliaries in asymmetric synthesis is attempted. 1. Introduction 2. Synthesis and Applications of [1,1′-binaphthyl]-2,2′-diol (1) and Derivatives 2.1. Synthesis 2.2. Applications 2.2.1. Enantioselective Reduction of Prochiral Ketones 2.2.2. Enantioselective Addition of Chiral Titanium Reagents to Aromatic Aldehydes 2.2.3. Asymmetric Diels-Alder Reactions 2.2.4. Asymmetric Hydrogenation of Prochiral Unsaturated Acids and Esters 2.2.5. Asymmetric Alkylation of Racemic Allylic Substrates 2.2.6. Crown Ethers Containing 1,1′-Binaphthylic Units 2.2.7. Stereoselective Polymerization 2.2.8. Asymmetric Ullmann Coupling Reactions 2.2.9. Asymmetric Alkylation of Arylacetic Acids 2.2.10. Asymmetric Cyclization 3. Synthesis and Applications of [1,1′-Binaphthyl]-2,2′-dithiol (2) 3.1. Synthesis 3.2. Applications 4. Synthesis and Applications of 2,2′-Bis(diarylphosphino)-1,1′-binaphthyls (BINAPs) 4.1. Synthesis 4.2. Applications 4.2.1. Rh(I)-BINAP Complexes 4.2.1.1. Asymmetric Hydrogenation of α-Acylaminoacrylic Acids 4.2.1.2. Asymmetric Isomerization of Double Bonds 4.2.1.3. Asymmetric Hydroboration of Styrenes 4.2.2. Ru(II)-BINAP Complexes 4.2.2.1. Asymmetric Hydrogenation of α,β- and β,γ-Unsaturated Acids 4.2.2.2. Asymmetric Hydrogenation of (Z)-2-Acyl-1-benzylidene-1,2,3,4-tetrahydroisoquinolines 4.2.2.3. Asymmetric Hydrogenation of Prochiral Allylic Alcohols 4.2.2.4. Asymmetric Hydrogenation of Chiral Allylic Secondary Alcohols 4.2.2.5. Asymmetric Hydrogenation of Prochiral Functionalized Ketones 4.2.2.6. Asymmetric Hydrogenation of β-Oxoesters 4.2.2.7. Asymmetric Hydrogenation of 1,3-Diketones 4.2.3. Pd-BINAP Complexes 5. Synthesis and Applications of [1,1′-Binaphthyl]-2,2′-diamine (4) and its Analogues 5.1. Synthesis 5.2. Applications 5.2.1. Enantioselective Reduction of Ketones 5.2.2. Asymmetric Hydrogenation of Acylaminoacrylic Acids 5.2.3. Asymmetric Synthesis of Lactones 5.2.4. Asymmetric Alkylation of Aromatic Aldehydes Mediated by N,N,N′,N′-Tetramethyl[1,1′-binaphthyl]-2, 2′-diamine (51) 6. Some Other 1,1′-Binaphthyl Derivatives with C ₂-Symmetry 6.1. 1,1′-Binaphthylic Substituted Tetramethylethylenediamine 6.2. 2,2′-Bis[(diphenylphosphino)methyl]-1,1′-binaphthyl [(S)-(-)-NAPHOS(1,1′)] 6.3. Miscellanea 7. Conclusions

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