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Catalytic Asymmetric Synthesis


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cinnamaldehyde and cyc...

      2 Chapter 5TABLE 5.1. Asymmetric α‐oxyaminaton of aldehyde and its variation.TABLE 5.2. Effect of helical part of peptide catalyst for enantioselective Fr...

      3 Chapter 12TABLE 12.1. C–H insertion into doubly allylic sites.TABLE 12.2. C–H insertion of THF.TABLE 12.3. C–H insertion of 1‐methoxybutane.TABLE 12.4. Synthesis of β‐lactones.TABLE 12.5. C–H amidation of indane and tetraline.TABLE 12.6. Synthesis of cyclic sulfamidates with iminoiodinane.TABLE 12.7. Intermolecular C–H amination with azides.TABLE 12.8. Synthesis of arylsulfonamides.TABLE 12.9. Synthesis of pyrrolidines.TABLE 12.10. Synthesis of sulfamides and sulfonamides.TABLE 12.11. Stereoselective C–H amination with N ‐(sulfonyloxy)carbamates....TABLE 12.12. Synthesis of γ‐lactams.

      4 Chapter 21TABLE 21.1. Binary catalyst systems based on chiral salenCo(III)X for racemi...

      List of Illustrations

      1 Chapter 1Figure 1.1. Representative organocatalysts.Figure 1.2. The reaction of enamines generated from diphenylprolinol silyl e...Figure 1.3. Nucleophilicity and electrophilicity of enamines and iminium ion...Scheme 1.1. Reactions of cinchona alkaloid catalysts.Figure 1.4. Transition state for the aldol reaction catalyzed by proline....Figure 1.5. Transition state of the Mannich reaction.Scheme 1.2. The reaction mechanism of the Michael reaction of aldehyde and n...Figure 1.6. Diarylprolinol silyl ether in this study.Scheme 1.3. The reaction mechanism of the Diels‐Alder reaction.Scheme 1.4. The reaction mechanism of the Michael reaction.Scheme 1.5. The reaction mechanism.Scheme 1.6. Stereodivergent α‐allylation of branched aldehydes using allyl a...Scheme 1.7. Stereodivergent α‐allylation of branched aldehydes using an alky...

      2 Chapter 2Figure 2.1. Examples of chiral Brønsted acids.Figure 2.2. pKa values of chiral Brønsted acids in DMSO by calculation.Figure 2.3. Effect of 3,3′‐substituents of BINOL‐derived phosphoric acid on ...Figure 2.4. Function of chiral phosphoric acid.Figure 2.5. Metal salts of chiral phosphoric acid.Scheme 2.1. Mannich reaction by Akiyama (a), and by Terada (b)Scheme 2.2. Mannich reaction with N‐(2‐hydroxyphenyl)‐imine (a) and with N‐p...Scheme 2.3. Mannich reaction of 2,4‐pentandione and N‐Cbz‐imine.Scheme 2.4. Mannich reaction between bisi‐silyl ketene acetal and silylated ...Scheme 2.5. Pictet‐Spengler reaction between tryptamine and aldehyde (a) (...Scheme 2.6. Addition of thiol.Scheme 2.7. Addition of hydrazone.Scheme 2.8. Polyene cyclization.Scheme 2.9. Friedel‐Crafts alkylation reaction between indoles and imines....Scheme 2.10. Friedel‐Crafts alkylation reaction with ketimines and indoles (...Scheme 2.11. Friedel‐Crafts alkylation reaction between N‐H trifluoromethyla...Scheme 2.12. Friedel‐Crafts alkylation reaction between indole and N‐H trifl...Scheme 2.13. Internal redox reaction.Scheme 2.14. Radical addition to imines.Scheme 2.15. Torgov reaction.Scheme 2.16. Prins cyclization.Scheme 2.17. Intramolecular carbonyl‐ene reaction.Scheme 2.18. Intermolecular carbonyl‐ene reaction.Scheme 2.19. Kinetic resolution of homoaldols.Scheme 2.20. Allylation of aldehyde by allylboronate (a) (), and propary...Figure 2.6. Transition state model of the allylation with allylboronate.Scheme 2.21. Allylation of aldehyde with γ‐silyl boronate.Scheme 2.22. Allylation of aldehydes with α‐vinyl allylboronate.Scheme 2.23. Reaction between di(boryl)butane and aldehyde, leading to the f...Scheme 2.24. Allylation reaction using 9c (a) and 11b,c (b) (Scheme 2.25. Mukaiyama aldol reaction with ketones (a) and ketone selective ...Figure 2.7. Reaction intermediate in the ketone‐selective reaction.Scheme 2.26. Enantioselective synthesis of isoindolinones.Scheme 2.27. Kinetic resolution of 2‐amido benzyl alcohols.Scheme 2.28. Oxa‐Pictet‐Spengler reaction of 2‐arylethanols.Scheme 2.29. Oxa‐Pictet‐Spengler reaction.Scheme 2.30. Oxa‐Pictet‐Spengler reaction between tryptophol and aldehydes....Scheme 2.31. Oxa‐Pictet‐Spengler reaction with ketal.Scheme 2.32. Diels‐Alder reaction.Scheme 2.33. Diels‐Alder reaction by C–H acid.Figure 2.8. Silylium binaphthyl‐allyl‐tetrasulfonate anion intermediate.Scheme 2.34. Diels‐Alder reaction between simple ester and cyclopentadiene c...Scheme 2.35. Diels–Alder reaction between cyclopentadien and enals (a), and ...Scheme