(1S,2R,4S)-N-Boc-1-氨基-2-羟基环戊烷-4-羧酸甲酯合成路线 （共 8 条）
反应条件
1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene(cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen in methanol T=20°C; P=3878.61 Torr;
参考文献
Lloyd, Richard C.; Lloyd, Michael C.; Smith, Mark E. B.; Holt, Karen E.; Swift, Jonathan P.; Keene, Philip A.; Taylor, Stephen J. C.; McCague, Raymond
Tetrahedron, 2004 , vol. 60, # 3 p. 717 - 728
反应条件
1.1: N-bromosuccinimide / tetrahydrofuran; H2O / 17 h / 20 °C 2.1: KOH / H2O; methanol / 48 h / 90 °C 2.2: tetrahydrofuran; H2O / 14 h / 20 °C / pH 10.5 3.1: triethylamine / methanol / 16 h / 0 - 20 °C 4.1: H2 / [(S,S)-(Me-DuPHOS)-Rh(COD)]BF4 / methanol / 14 h / 20 °C / 3750.38 Torr View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
反应条件
1: triethylamine / methanol / 16 h / 0 - 20 °C 2: H2 / [(S,S)-(Me-DuPHOS)-Rh(COD)]BF4 / methanol / 14 h / 20 °C / 3750.38 Torr View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
反应条件
1.1: KOH / H2O; methanol / 48 h / 90 °C 1.2: tetrahydrofuran; H2O / 14 h / 20 °C / pH 10.5 2.1: triethylamine / methanol / 16 h / 0 - 20 °C 3.1: H2 / [(S,S)-(Me-DuPHOS)-Rh(COD)]BF4 / methanol / 14 h / 20 °C / 3750.38 Torr View Scheme
参考文献
Lloyd, Richard C.; Lloyd, Michael C.; Smith, Mark E. B.; Holt, Karen E.; Swift, Jonathan P.; Keene, Philip A.; Taylor, Stephen J. C.; McCague, Raymond
Tetrahedron, 2004 , vol. 60, # 3 p. 717 - 728
反应条件
1.1: KOH / H2O; methanol / 48 h / 90 °C 1.2: tetrahydrofuran; H2O / 14 h / 20 °C / pH 10.5 2.1: triethylamine / methanol / 16 h / 0 - 20 °C 3.1: H2 / [(S,S)-(Me-DuPHOS)-Rh(COD)]BF4 / methanol / 14 h / 20 °C / 3750.38 Torr View Scheme
参考文献
Lloyd, Richard C.; Lloyd, Michael C.; Smith, Mark E. B.; Holt, Karen E.; Swift, Jonathan P.; Keene, Philip A.; Taylor, Stephen J. C.; McCague, Raymond
Tetrahedron, 2004 , vol. 60, # 3 p. 717 - 728
反应条件
1.1: 85 percent / SOCl2 / 2 h / 0 - 20 °C 2.1: 96 percent / NEt3 / CH2Cl2 / 2 h / 0 °C 3.1: NBS / tetrahydrofuran; H2O / 20 °C 4.1: KOH / methanol; H2O / 90 °C 4.2: H2O; tetrahydrofuran / 5 - 20 °C / pH 10.5 5.1: NEt3 / methanol / 5 - 20 °C 6.1: H2; {(S,S)-[MeDuPHOS]-Rh(COD)}BF4 / methanol / 20 °C / 3878.61 Torr View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
反应条件
1.1: lactamase / Enzymatic reaction 2.1: 85 percent / SOCl2 / 2 h / 0 - 20 °C 3.1: 96 percent / NEt3 / CH2Cl2 / 2 h / 0 °C 4.1: NBS / tetrahydrofuran; H2O / 20 °C 5.1: KOH / methanol; H2O / 90 °C 5.2: H2O; tetrahydrofuran / 5 - 20 °C / pH 10.5 6.1: NEt3 / methanol / 5 - 20 °C 7.1: H2; {(S,S)-[MeDuPHOS]-Rh(COD)}BF4 / methanol / 20 °C / 3878.61 Torr View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
反应条件
1.1: triethylamine; DMAP / CH2Cl2 / 0.75 h / 0 °C 2.1: KOAc / dimethylformamide / 72 h / 60 °C 2.2: NaOMe / methanol / 7 h / 0 °C View Scheme
参考文献
Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond
Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705
