Synthesis and catalytic properties of diverse chiral polyamines.
Chiral polyamines can be utilized for a variety of potential applications, ranging from asymmetric catalysis to nonviral gene delivery systems for DNA and RNA. They can also be utilized to solubilize carbon nanotubes. Thus, methods for the straightforward synthesis of chiral polyamines are needed. We present herein two synthetic strategies for accessing chiral polyamines. The potential of these chiral amines to catalyze two organic reactions with a high degree of chiral induction was also explored.Text: Chiral polyamines have been utilized for a variety of applications. First, polyamines are polycationic at neutral pH; as such, they interact strongly with both DNA and RNA.1 They can therefore be utilized as effective nonviral gene delivery agents.2 Second, chiral polyamines are efficient catalysts for various organic transformations.3 Polyamines have also been used to solubilize carbon nanotubes.4 Finally, chiral polyamines are excellent ligands for many transition metals.5 Due to their numerous applications, high-yielding synthetic strategies for their preparation are in great demand. We present herein two synthetic strategies for accessing chiral polyamines, and the potential of these chiral amines to catalyze two organic reactions.
Levine
Mindy
M
Columbia University, Department of Chemistry, 3000 Broadway, New York 10027, USA.
Kenesky
Craig S
CS
Zheng
Shengping
S
Quinn
Jordan
J
Breslow
Ronald
R