Catalytic Asymmetric Synthesis

17 Chapter 17Scheme 17.1. Pd‐catalyzed asymmetric allylic alkylation of α‐nitro esters wi...Scheme 17.2. (a) Enantio‐ and diastereoselective deracemization of cis ‐2‐oxa...Scheme 17.3. Oxidative and redox neutral Pd‐catalyzed allylic arylation with...Scheme 17.4. Pd‐catalyzed asymmetric allylic alkylation with vinylcyclopropa...Scheme 17.5. Hydroxyacrylate nucleophiles in the Pd‐catalyzed asymmetric all...Scheme 17.6. Pd‐catalyzed DYKAT of benzylic diarylmethyl carbonates.Scheme 17.7. Asymmetric allylic alkylation with Mortia–Baylis–Hillman adduct...Scheme 17.8. Pd‐catalyzed asymmetric allylic fluoroalkylation of cyclic ally...Scheme 17.9. Dearomative C 2selective allylic alkylation of pyrrole nucleoph...Scheme 17.10. Pd‐catalyzed asymmetric allylic alkylation of in situ generate...Scheme 17.11. Allylic alkylation of enols with allyl alcohol via CO 2activat...Scheme 17.12. Cu/Pd dual catalysis for the asymmetric allylic alkylation of ...Scheme 17.13. Pd/Cu dual catalysis for enantio‐ and diastereodivergent allyl...Scheme 17.14. Merger of photoredox catalysis and Pd‐catalyzed enantioselecti...Figure 17.1. Enantioenriched motifs accessed by Stoltz via decarboxylative a...Figure 17.2. Substrate classes prepared via Pd‐catalyzed decarboxylative all...Scheme 17.15. Asymmetric decarboxylative propargylation of α‐aryl indanones....Scheme 17.16. Michael acceptor interrupted Pd‐catalyzed allylic alkylation....Scheme 17.17. Decarboxylative allylic alkylation of benzoxazolinone‐derived ...Scheme 17.18. (a) Acyclic stereocontrol in amides.(b) Acyclic stereocont...Scheme 17.19. Ni‐catalyzed asymmetric allylic alkylation of diarylmethanes a...Scheme 17.20. Ni‐catalyzed allylic alkylation of cyclic β‐ketoesters with un...Scheme 17.21. Ni‐catalyzed allylic alkylation of α‐acyl lactones with unacti...Scheme 17.22. Ni‐catalyzed allylic alkylation of cyclic β‐ketoesters with N ‐...Scheme 17.23. Ni‐catalyzed allylic alkylation of acyclic acyl imidazoles wit...Scheme 17.24. Ni‐catalyzed Suzuki‐type cross‐coupling of pro‐quinolinium ele...Scheme 17.25. Mo‐catalyzed allylic alkylation of acyclic α‐cyanoesters.Scheme 17.26. (a) Cyclopentadienyl ruthenium complex catalyzed allylic alkyl...Scheme 17.27. (a) Rh‐catalyzed DYKAT of cyclic allylic bromides and chloride...Scheme 17.28. (a) Enantioselective Rh‐catalyzed allylic alkylation of acycli...Scheme 17.29. (a) Rh‐catalyzed allylic alkylation of 1,3‐diketones with ally...Scheme 17.30. (a) Ir‐catalyzed allylic alkylation of 3‐fluorosubstituted ele...Scheme 17.31. (a) First report of an MAC nucleophile in the Ir‐catalyzed all...Scheme 17.32. Counterion‐controlled diastereoselective Ir‐catalyzed allylic ...Scheme 17.33. (a) Diastereo‐ and enantioselective allylic alkylation of 5 H ‐o...Scheme 17.34. (a) Ir‐catalyzed allylic alkylation of cyclic β‐ketoesters. (b...Scheme 17.35. Ir‐catalyzed regio‐, diastereo‐, and enantioselective allylic ...Scheme 17.36. (a) Tandem Ir‐catalyzed allylic alkylation/Cope rearrangement....Scheme 17.37. Ir‐catalyzed enantioselective allylic alkylation with crotyl c...Scheme 17.38. Stereodivergent Ir‐catalyzed catalyzed allylic alkylation via ...Scheme 17.39. Ir‐catalyzed allylic alkylation of trimethylsiloxy furan.Scheme 17.40. Diastereo‐ and enantioselective allylic alkylation of non‐stab...Scheme 17.41. Dual‐catalytic stereodivergence in the Ir‐catalyzed allylic al...Scheme 17.42. Desymmetrizing CADA of bisphenol derivatives.Scheme 17.43. Allyl–olefin coupling via Ir‐catalyzed allylic substitution....Scheme 17.44. Ir‐catalyzed allylic alkylation with functionalized organozinc...Scheme 17.45. Formal umpolung allylation of N ‐fluorenyl imines.Scheme 17.46. Cu‐catalyzed allylic alkylation of organolithium reagents.Scheme 17.47. (a) Cu‐catalyzed asymmetric allylic alkylation of allylic chlo...Scheme 17.48. (a) Enantioselective allylic arylation of allylic bromides to ...Scheme 17.49. (a) Enantioselective allylic alkylation of alkynylaluminum for...Scheme 17.50. Cu‐catalyzed enantioselective allylic alkylation with organobo...Scheme 17.51. Cu‐catalyzed asymmetric allylic allenylation with bench‐stable...Scheme 17.52. Cu‐catalyzed allylic alkylation of alkyl boranes with Z ‐allyli...Scheme 17.53. Dynamic kinetic asymmetric allylic alkylation of alkylzirconiu...Scheme 17.54. Cu‐catalyzed allylic alkylation with terminal alkyne nucleophi...Scheme 17.55. Cu‐catalyzed allylic alkylation of formidyl cuprates.Scheme 17.56. Cu‐catalyzed enantioselective allylic alkylation of γ‐butyrola...Scheme 17.57. First example of a highly enantio‐ and regioselective Co‐catal...Scheme 17.58. Enantio‐ and regioselective Co‐catalyzed allylic alkylation of...Scheme 17.59. Organophotoredox approach to Co‐catalyzed enantioselective all...

18 Chapter 18Scheme 18.1. Carbometallation of alkynes and alkenes.Scheme 18.2. Asymmetric carbometallation of alkenes.Scheme 18.3. ZACA reactions of allyl alcohols.Scheme 18.4. ZACA reactions of tert ‐butyldimethylsilyl‐protected terminal al...Scheme 18.5. ZACA reactions of unfunctionalized alkenes.Scheme 18.6. Zirconium‐catalyzed inter‐ and intramolecular double carboalumi...Scheme 18.7. Copper‐catalyzed carbometallation of cyclopropenes with vinylal...Scheme 18.8. Palladium‐catalyzed carbozincation of spirocyclopropenes.Scheme 18.9. Palladium‐catalyzed carbozincation of 3,3‐disubstituted cyclopr...Scheme 18.10. Copper‐catalyzed carbozincation of 3,3‐disubstituted cycloprop...Scheme 18.11. Copper‐catalyzed carbomagnesiation of 3,3‐disubstituted cyclop...Scheme 18.12. Copper‐catalyzed carbomagnesiation of 3,3‐disubstituted cyclop...Scheme 18.13. Palladium‐catalyzed and carbopalladation‐initiated carbocycliz...Scheme 18.14. Palladium‐catalyzed intramolecular carboiodination.Scheme 18.15. Palladium‐catalyzed intramolecular reductive Heck reactions.Scheme 18.16. Palladium‐catalyzed intramolecular arylative dearomatization o...Scheme 18.17. Palladium‐catalyzed intramolecular carboiodination‐isocyanide ...Scheme 18.18. Palladium‐catalyzed intramolecular reductive Heck reactions us...Scheme 18.19. Palladium‐catalyzed vinylborylation of ( Z )‐1‐iododienes with b...Scheme 18.20. Palladium‐catalyzed arylalkynylation of indoles.Scheme 18.21. Palladium‐catalyzed dearomative arylborylation of indoles.Scheme 18.22. Palladium‐catalyzed intramolecular carbonylative Heck reaction...Scheme 18.23. Palladium‐catalyzed tandem intramolecular Heck insertion and T...Scheme 18.24. Palladium‐catalyzed Heck reactions of acyclic alkenyl fluoride...Scheme 18.25. Palladium‐catalyzed tandem Heck insertion and Sonogashira coup...Scheme 18.26. Palladium‐catalyzed hydroalkynylation of 3,3‐disubstituted cyc...Scheme 18.27. Nickel‐catalyzed intramolecular carboiodination of alkenes wit...Scheme 18.28. Nickel‐catalyzed intramolecular intramolecular Mizoroki–Heck c...Scheme 18.29. Nickel‐catalyzed intramolecular dearomative and reductive Heck...Scheme 18.30. Nickel‐catalyzed intramolecular carboiodination of alkenes wit...Scheme 18.31. Nickel‐catalyzed carbocyclization of tethered allene–ketone wi...Scheme 18.32. Rhodium‐catalyzed carborhodation of cyclopent‐2‐ene‐1,4‐diethy...Scheme 18.33. Rhodium‐catalyzed arylation of azabicyclic alkene with arylbor...Scheme 18.34. Rhodium‐catalyzed arylation of β‐Substituted alkenyl‐ para ‐nitr...Scheme 18.35. Rhodium‐catalyzed tandem ring‐opening and intramolecular C–O c...Scheme 18.36. Rhodium‐catalyzed arylation of 3,3‐disubstituted cyclopropenes...Scheme 18.37. Rhodium‐catalyzed arylation of 2 H ‐chromenes with aryl boronic ...Scheme 18.38. Rhodium‐catalyzed carbozincation of 1,6‐enynes with ArZnCl.Scheme 18.39. Cobalt‐catalyzed alkynylation of 1,1‐disubstituted allenes wit...Scheme 18.40. Cobalt‐catalyzed hydroborative cyclization of amide‐tethered 1...Scheme 18.41. Cobalt‐catalyzed hydroborative cyclization of anilide‐tethered...Scheme 18.42. Cobalt‐catalyzed hydroalkylation of oxabicyclic alkenes with c...