| Host-Guest chemistry is an emerging area of interest. Many structurally diverse hosts have been devised and synthesized that demonstrates varying degrees of binding selectivity.; A new ring system was designed as a useful component of such synthetic receptors. Topologically related to Troger's base and Kagan's ether, this new structure has multiple attachment points, a well defined chiral surface, a hydrophobic concavity and a very hydrophilic convexity. This new structural element of well-defined geometry, inherent desirable solubility and polarity, bearing multiple functional groups, is expected to lead to unique new host structures. We have reported successful preparation of the new ring system from readily available starting materials in good yield. A one-pot process leads to menthyl phosphinate formation, followed by double addition to aldehyde, rapidly forming diadduct in high yield. After reduction to diamine in 92% yield, another multiple reaction leads in one step from the many diastereomers of diamine to the two diastereomers of desired target structure in high yield, again with losses in purification leading to isolation of pure 51 in 54% yield. Overall, this complex structure is obtained in three operations in 34% yield from readily available starting materials.; We anticipate applications of this ring system in Host-Guest chemistry and transition metal catalysis. |
