Cyclohexane, trans-1,2-diamino-.

The reductive amination of ketones can be carried out under hydrogen pressure in the presence of palladium catalysts. However, if enantiopure Q -aminoketones are used, partial racemization of the intermediate a-amino imine can occur, owing to the equilibration with the corresponding enam-ine [102]. Asymmetric hydrogenation of racemic 2-amidocyclohexanones 218 with Raney nickel in ethanol gave a mixture of cis and trans 1,2-diamino cyclohexane derivatives 219 in unequal amounts, presumably because the enamines are intermediates, but with excellent enantioselectivity. The two diastereomers were easily separated and converted to the mono-protected cis- and trans- 1,2-diaminocyclohexanes 220. The receptor 221 has been also synthesized by this route [103] (Scheme 33). 

Figure 58 Partial 13C NMR spectra for (R,R)-trans-1,2- diaminocyclohexane-( )-irani-l, 2-cyclopentanediol and (R)-l,l -bi-2-naphthol adducts. Left (a) (R,R)-trans-1, 2-diaminocy-clohexane (b) inms-( )cyclopentanediol (c) 1 1 adduct between (R,R)-trans-1, 2-diamino-cyclohexane and tranx-( )-cyclopentanediol (d) 0.5 1 adduct between (R,R)-trans-1, 2-diaminocyclohexane and Znms-(+/-)-cyclopentanediol. Right (a) (R,R)-trans-1, 2-diami-nocyclohexane (b) 1 1 adduct between (i )-l,l -bi-2-naphthol and trans-( )-1, 2-diaminocyclohexane (c) 1 1 adduct between R,R)-trans-1, 2-diaminocyclohexane and (2 )-1,1 -bi-2-naphthol (e.e. 35%) showing molecular recognition and chiral discrimination of the diastereomeric supraminols (d) 1 1 adduct between (R)-l,l -bi-2-naphthol and (R,R)-trans-1, 2-diaminocyclohexane [60],...

Chaney and co-workers investigated the in vitro biotransformations of oxaliplatin and other Pt-DNA adducts containing trans-(7, 7 )-1,2-diamino-cyclohexane carrier ligand in rat blood by H-isotope tracing and found that their decay in the plasma ultrafiltrate occurred rapidly (t < 1 h). Size-exclusion HPLC coupled on-line to ICP-MS was utilized to directly monitor early protein biotransformations of Pt-labeled oxaliplatin following its intravenous administration to cancer patients. It was found that oxaliplatin is almost equally bound to y-globulins and albumin (40% of the Pt bound respectively), in consistence with a previous in vitro study. ... 

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