An efficient chemoenzymatic method to prepare optically active primary-tertiary trans-cycloalkane-1,2-diamines

作者：Javier Quijada F; Gonzalez Sabin Javier; Rebolledo Francisca^*; Gotor Vicente

来源：Tetrahedron, 2009, 65(38): 8028-8034.

DOI：10.1016/j.tet.2009.07.035

• Vicinal diamines
• Lipase
• Aminolysis

Optically active trans-N-Boc-cyclopentane- and cyclohexane-1,2-diamines (7) were prepared by a chemoenzymatic method from the corresponding (+/-)-trans-N,N-diallylcycloalkane-1,2-diamine. These mono-carbamates 7 (ee=99%) were used as the starting materials in the syntheses of different vicinal primary-tertiary diamines. Thus, by means of a simple three-step sequence involving a reductive-amination of an aromatic aldehyde with 7, N-methylation and finally, cleavage of the Boc group, several trans-N-(arylmethyl)-N-methylcyclopentane- and cyclohexane-1,2-diamines were obtained in high yields.

• 出版日期2009-9-19