CHEMOENZYMATIC SYNTHESES OF POLYAMINES AND TETRAAZAMACROCYCLES
摘要:
Syntheses of different open chain polyamines starting from enzymatically prepared bis(amidoesters) are described. Some of these polyamines are also used as precursors in the syntheses of tetraazamacrocycles. This methodology cart also be applied to the synthesis of chiral compounds.
Abstract N,N'-substituted symmetrical diamines are readily prepared in high yields in a one-pot procedure from diazidoalcanes and dichloroboranes. This approach has been extended to the synthesis of thermine, a tetramine isolated from Thermus Thermophilus.
Aliphatic amino azides as key building blocks for efficient polyamine syntheses
作者:Bertrand Carboni、Aziza Benalil、Michel Vaultier
DOI:10.1021/jo00066a028
日期:1993.7
New routes to open-chain polyamines have been developed using aliphatic amino azides as common precursors for the construction of the carbon-nitrogen framework. These alpha,omega-diaminoalkane synthetic equivalents were combined with (omega-halogenoalkyl)dichloroboranes to extend the polyamine chain from the azido moiety. An extension from the free amino group can also be achieved via a Michael type addition with acrylonitrile or a reductive amination with a gamma-azido ketone. Further transformations led to a large variety of regioselectively C- or (and) N-substituted polyamines.