| 摘要 |
Preparing GSK1360707 ((1R,6S)-1-(3,4-dichlorophenyl)-6-(methoxymethyl)-4-azabicyclo[4.1.0]heptane) (I) and related compounds having 6-aryl-1-[(alkyloxy)alkyl]-3-azabicyclo[4.1.0]heptane skeleton, and their salts in optically active form by an asymmetric gold-catalyzed cycloisomerization, comprises converting enyne compounds (II) to substituted (3-azabicyclo[4.1.0]hept-4-en-1-yl)-methanol derivatives (III) in presence of chiral gold complexes (IV) or chiral silver complexes (V). Preparing GSK1360707 ((1R,6S)-1-(3,4-dichlorophenyl)-6-(methoxymethyl)-4-azabicyclo[4.1.0]heptane) (I) and related compounds having 6-aryl-1-[(alkyloxy)alkyl]-3-azabicyclo[4.1.0]heptane skeleton, and their salts in optically active form by an asymmetric gold-catalyzed cycloisomerization, comprises converting enyne compounds of formula (R1-CC-CH 2-N(R3)-CH 2-C(=CH 2)-CH 2-OR2) (II) to substituted (3-azabicyclo[4.1.0]hept-4-en-1-yl)-methanol derivatives of formula (III) in presence of chiral gold complexes of formula (L-Au-Y1) (IV) or chiral silver complexes of formula (Ag-X) (V). R1, R6 : 1-12C aryl; either R2, R9, R10 : 1-6C alkyl; or R9+R10 : five-membered ring; R3 : -C(O)OR4 or -SO 2R5; either R4, R5, R7, R8 : 1-6C alkyl or 1-12C aryl; or R7+R8 : 5-8 membered ring; L : chiral monodentate phosphorus moiety of formula (VI); Z : O or NR8; X : BF 4, SbF 6, B((1-6C aryl) 4), Al((O-1-6C alkyl) 4), OSO 2CF 3(=triflate), OSO 2(1-6C alkyl), OSO 2(1-12C aryl), N(triflate) 2, C(triflate) 3, NO 3or F; and Y1 : halo. [Image] ACTIVITY : Antidepressant. No biological data given. MECHANISM OF ACTION : Serotonin-Norepinephrine-Dopamine reuptake inhibitor/Triple reuptake inhibitor. |
