首页 关于有机合成中串联反应（cascade reactions）的诠释

关于有机合成中串联反应（cascade reactions）的诠释

关于有机合成中串联反应（cascade reactions）的诠释 OH H O BURIED TREASURES: CASCADES WE HAVEN'T SEEN N O O O O OH HO HO H O MeNH2 R. Robinson, J. Chem. Soc., 1917, 762 O O Me H Me H H H Ph H H H H H CO2MeH O H CH3 O H3C H3C H HO H H H H H CH3 Cascades Articulated Main Ent...

OH H O BURIED TREASURES: CASCADES WE HAVEN'T SEEN N O O O O OH HO HO H O MeNH2 R. Robinson, J. Chem. Soc., 1917, 762 O O Me H Me H H H Ph H H H H H CO2MeH O H CH3 O H3C H3C H HO H H H H H CH3 Cascades Articulated Main Entry: 1cas·cade Pronunciation: (")kas-'kAd Function: noun Etymology: French, from Italian cascata, from cascare to fall, from (assumed) Vulgar Latin casicare, from Latin casus fall, Date: 1641 1: a steep usually small fall of water; especially :one of a series 2a : something arranged or occurring in a series or in a succession of stages so that each stage derives from or acts upon the product of the preceding b: a fall of material (as lace) that hangs in a zigzag line 3: something falling or rushing forth in quantity 4: One-pot, sequential reactions involving more than one intermediate, preferrably 1) leading to an increase in molecular complexity and 2) without changing reaction conditions see: Chem. Commun., 2003, 551 Cascades Articulated Main Entry: 1cas·cade Pronunciation: (")kas-'kAd Function: noun Etymology: French, from Italian cascata, from cascare to fall, from (assumed) Vulgar Latin casicare, from Latin casus fall, Date: 1641 1: a steep usually small fall of water; especially :one of a series 2a : something arranged or occurring in a series or in a succession of stages so that each stage derives from or acts upon the product of the preceding b: a fall of material (as lace) that hangs in a zigzag line 3: something falling or rushing forth in quantity 4: One-pot, sequential reactions involving more than one intermediate, preferrably 1) leading to an increase in molecular complexity and 2) without changing reaction conditions see: Chem. Commun., 2003, 551 CO2Me PhH H H H H CO2MeH 1) H2, Pd/BaSO4 quinoline 2) toluene, 100 °C 3 intermediates Me OH Me Me 1,2-dichloroethane; K2CO3, H2O, MeOH 2 intermediates OO O , TFA, O Me Me Me H Me H HH OP1 H P2O O H CH3 O H3C H3C H P1O H H H H H CH3 RO H3C PO OP OP CH3 O O OR SePh mCPBA, CH2Cl2; 40 °C, CHCl3 4 intermediates Some Inspiration Nicolaou, K. C., J. Amer. Chem. Soc., 1982, 5555 Ph Johnson, W. S., J. Amer. Chem. Soc., 1971, 4330 Sorensen, E. J., J. Amer. Chem. Soc., 2002, 4552 CO2Me PhH H H H H CO2MeH 1) H2, Pd/BaSO4 quinoline 2) toluene, 100 °C 3 intermediates Me OH Me Me 1,2-dichloroethane; K2CO3, H2O, MeOH 2 intermediates OO O , TFA, O Me Me Me H Me H HH OP1 H P2O O H CH3 O H3C H3C H P1O H H H H H CH3 RO H3C PO OP OP CH3 O O OR SePh mCPBA, CH2Cl2; 40 °C, CHCl3 4 intermediates Some Inspiration Nicolaou, K. C., J. Amer. Chem. Soc., 1982, 5555 Ph Johnson, W. S., J. Amer. Chem. Soc., 1971, 4330 Sorensen, E. J., J. Amer. Chem. Soc., 2002, 4552 CO2Me PhH H H H H CO2MeH 1) H2, Pd/BaSO4 quinoline 2) toluene, 100 °C 3 intermediates Me OH Me Me 1,2-dichloroethane; K2CO3, H2O, MeOH 2 intermediates OO O , TFA, O Me Me Me H Me H HH OP1 H P2O O H CH3 O H3C H3C H P1O H H H H H CH3 RO H3C PO OP OP CH3 O O OR SePh mCPBA, CH2Cl2; 40 °C, CHCl3 4 intermediates Some Inspiration Nicolaou, K. C., J. Amer. Chem. Soc., 1982, 5555 Ph Johnson, W. S., J. Amer. Chem. Soc., 1971, 4330 Sorensen, E. J., J. Amer. Chem. Soc., 2002, 4552 N H O OPh O EtO N H O H H O EtO O Ph O , hu Dihydropyridone Synthesis N O O O H H H N O OH O MeO2C Ph PhMeO2C N O O Ph MeO2C N O OHO H H MeO2C Ph O H Chem. Pharm. Bull., 1987, 4730 -CO N H O OPh O EtO N H O H H O EtO O Ph O , hu Dihydropyridone Synthesis N O O O H H H N O OH O MeO2C Ph PhMeO2C N O O Ph MeO2C N O OHO H H MeO2C Ph O H Chem. Pharm. Bull., 1987, 4730 -CO N H O OPh O EtO N H O H H O EtO O Ph O , hu Dihydropyridone Synthesis N O O O H H H N O OH O MeO2C Ph PhMeO2C N O O Ph MeO2C N O OHO H H MeO2C Ph O H Chem. Pharm. Bull., 1987, 4730 -CO N O O O H H H MeO2C Ph N H O OPh O EtO N H O H H O EtO O Ph O , hu Dihydropyridone Synthesis N O O O H H H N O OH O MeO2C Ph PhMeO2C N O O Ph MeO2C N O OHO H H MeO2C Ph O H Chem. Pharm. Bull., 1987, 4730 -CO N H O OPh O EtO N H O H H O EtO O Ph O , hu Dihydropyridone Synthesis N O O O H H H N O OH O MeO2C Ph PhMeO2C N O O Ph MeO2C N O OHO H H MeO2C Ph O H Chem. Pharm. Bull., 1987, 4730 -CO N H O OPh O EtO N H O H H O EtO O Ph O , hu Dihydropyridone Synthesis N O O O H H H N O OH O MeO2C Ph PhMeO2C N O O Ph MeO2C N O OHO H H MeO2C Ph O H Chem. Pharm. Bull., 1987, 4730 -CO Degredation to a Cyclohexadiene Br Br HHCH3Li Et2O Angew. Chem. Int. Ed., 1975, 765. CH3Li Degredation to a Cyclohexadiene Br Br HHCH3Li Et2O Angew. Chem. Int. Ed., 1975, 765. CH3Li Degredation to a Cyclohexadiene Br Br HHCH3Li Et2O Angew. Chem. Int. Ed., 1975, 765. CH3Li Degredation to a Cyclohexadiene Br Br HHCH3Li Et2O Angew. Chem. Int. Ed., 1975, 765. CH3Li Degredation to a Cyclohexadiene Br Br HHCH3Li Et2O Angew. Chem. Int. Ed., 1975, 765. CH3Li Starting Material? Br Br H H Li Br CH2I2, Zn/Cu CHBr3, KOtBu MeLi Et2O 1. CH2I2, Zn/Cu 2. CHBr3 3. MeLi, Et2O Angew. Chem. Intern. Ed., 1975, 496 Starting Material? Br Br H H Li Br CH2I2, Zn/Cu CHBr3, KOtBu MeLi Et2O 1. CH2I2, Zn/Cu 2. CHBr3 3. MeLi, Et2O Angew. Chem. Intern. Ed., 1975, 496 Starting Material? Br Br H H Li Br CH2I2, Zn/Cu CHBr3, KOtBu MeLi Et2O 1. CH2I2, Zn/Cu 2. CHBr3 3. MeLi, Et2O Angew. Chem. Intern. Ed., 1975, 496 Starting Material? Br Br H H Li Br CH2I2, Zn/Cu CHBr3, KOtBu MeLi Et2O 1. CH2I2, Zn/Cu 2. CHBr3 3. MeLi, Et2O Angew. Chem. Intern. Ed., 1975, 496 Starting Material? Br Br H H Li Br CH2I2, Zn/Cu CHBr3, KOtBu MeLi Et2O 1. CH2I2, Zn/Cu 2. CHBr3 3. MeLi, Et2O Angew. Chem. Intern. Ed., 1975, 496 Synthesis of a Tetrayne AcO H BuLi; CuCl AcO Li Cu AcO Cu+ Cu+ BuLi Symmetry Forbidden Tetrahedron Lett., 1976, 2663 Synthesis of a Tetrayne AcO H BuLi; CuCl AcO Li Cu AcO Cu+ Cu+ BuLi Symmetry Forbidden Tetrahedron Lett., 1976, 2663 Synthesis of a Tetrayne AcO H BuLi; CuCl AcO Li Cu AcO Cu+ Cu+ BuLi Symmetry Forbidden Tetrahedron Lett., 1976, 2663 Synthesis of a Tetrayne AcO H BuLi; CuCl AcO Li Cu AcO Cu+ Cu+ BuLi Symmetry Forbidden Tetrahedron Lett., 1976, 2663 Synthesis of a Tetrayne AcO H BuLi; CuCl AcO Li Cu AcO Cu+ Cu+ BuLi Symmetry Forbidden Tetrahedron Lett., 1976, 2663 Complex Polycycle SiMe3HO HO Br SnBu3Bu3Sn Pd(PPh3)4 PhH, D SiMe3HO HO PdLnBr SiMe3HO HO PdLnBr SiMe3HO HO SnBu3 OH H HO SiMe3 Oxidative Addition Migratory Insertion Transmetallation SnBu3 Bu3Sn J. Am. Chem. Soc., 2001, 12107 Complex Polycycle SiMe3HO HO Br SnBu3Bu3Sn Pd(PPh3)4 PhH, D SiMe3HO HO PdLnBr SiMe3HO HO PdLnBr SiMe3HO HO SnBu3 OH H HO SiMe3 Oxidative Addition Migratory Insertion Transmetallation SnBu3 Bu3Sn J. Am. Chem. Soc., 2001, 12107 Complex Polycycle SiMe3HO HO Br SnBu3Bu3Sn Pd(PPh3)4 PhH, D SiMe3HO HO PdLnBr SiMe3HO HO PdLnBr SiMe3HO HO SnBu3 OH H HO SiMe3 Oxidative Addition Migratory Insertion Transmetallation SnBu3 Bu3Sn J. Am. Chem. Soc., 2001, 12107 Complex Polycycle SiMe3HO HO Br SnBu3Bu3Sn Pd(PPh3)4 PhH, D SiMe3HO HO PdLnBr SiMe3HO HO PdLnBr SiMe3HO HO SnBu3 OH H HO SiMe3 Oxidative Addition Migratory Insertion Transmetallation SnBu3 Bu3Sn J. Am. Chem. Soc., 2001, 12107 Complex Polycycle Cont... OH H HO SiMe3 SiMe3HO HO SnBu3H SiMe3 OH HO H SiMe3 O H O H - - SiMe3HO HO SnBu3 6 e- disrotatory 1H transfer J. Am. Chem. Soc., 2001, 12107 SiMe3HO HO SnBu3H SiMe3HO HO SnBu3H Complex Polycycle Cont... OH H HO SiMe3 SiMe3HO HO SnBu3H SiMe3 OH HO H SiMe3 O H O H - - SiMe3HO HO SnBu3 6 e- disrotatory 1H transfer J. Am. Chem. Soc., 2001, 12107 A [3.2.0] Bicycle J. Org. Chem., 1994, 8092 H O MeO2C H OTBDPS H CO2Me OTMS I TBDPSO H TMSI, (TMS)2NH OH TBDPSO CO2Me H SiMe3 N+ H TMS TMS I- OH TBDPSO CO2Me H TMS OHTBDPSO H I OMe O TMS2NH Si I I A [3.2.0] Bicycle J. Org. Chem., 1994, 8092 H O MeO2C H OTBDPS H CO2Me OTMS I TBDPSO H TMSI, (TMS)2NH OH TBDPSO CO2Me H SiMe3 N+ H TMS TMS I- OH TBDPSO CO2Me H TMS OHTBDPSO H I OMe O TMS2NH Si I I A [3.2.0] Bicycle J. Org. Chem., 1994, 8092 H O MeO2C H OTBDPS H CO2Me OTMS I TBDPSO H TMSI, (TMS)2NH OH TBDPSO CO2Me H SiMe3 N+ H TMS TMS I- OH TBDPSO CO2Me H TMS OHTBDPSO H I OMe O TMS2NH Si I I A [3.2.0] Bicycle J. Org. Chem., 1994, 8092 H O MeO2C H OTBDPS H CO2Me OTMS I TBDPSO H TMSI, (TMS)2NH OH TBDPSO CO2Me H SiMe3 N+ H TMS TMS I- OH TBDPSO CO2Me H TMS OHTBDPSO H I OMe O TMS2NH Si I I A [3.2.0] Bicycle J. Org. Chem., 1994, 8092 H O MeO2C H OTBDPS H CO2Me OTMS I TBDPSO H TMSI, (TMS)2NH OH TBDPSO CO2Me H SiMe3 N+ H TMS TMS I- OH TBDPSO CO2Me H TMS OHTBDPSO H I OMe O TMS2NH Si I I A [3.2.0] Bicycle J. Org. Chem., 1994, 8092 H O MeO2C H OTBDPS H CO2Me OTMS I TBDPSO H TMSI, (TMS)2NH OH TBDPSO CO2Me H SiMe3 N+ H TMS TMS I- OH TBDPSO CO2Me H TMS OHTBDPSO H I OMe O TMS2NH Si I I A Hydrindane Unpublished O O O PPh3H H O O H H H H O PhH, D PPh3 O P(O)Ph3 A Hydrindane Unpublished O O O PPh3H H O O H H H H O PhH, D PPh3 O P(O)Ph3 A Hydrindane Unpublished O O O PPh3H H O O H H H H O PhH, D PPh3 O P(O)Ph3 Another (the same) Hydrindane Hoye, T., Unpublished OHBn OBn OHBn OHBn H H H Bn Bn H HHO HO H HHHO Bn H H Grubbs Another (the same) Hydrindane Hoye, T., Unpublished OHBn OBn OHBn OHBn H H H Bn Bn H HHO HO H HHHO Bn H H Grubbs Another (the same) Hydrindane Hoye, T., Unpublished OHBn OBn OHBn OHBn H H H Bn Bn H HHO HO H HHHO Bn H H Grubbs N H O OPh O EtO N H O H H O EtO O Ph O , hu Br Br HH CH3Li Et2O AcO H BuLi; CuCl SiMe3HO HO Br SnBu3Bu3Sn Pd(PPh3)4 PhH, D OH H HO SiMe3 H CO2Me OTMS I H (TMS)2NH TMSI OTBDPS H O H OTBDPS MeO2C OHBn OBn H H Grubbs MeLi, Et2OBr Br O O O PPh3H H H H O PhH, D Summary

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