Wydział Chemii

Sebastian Koniarz

Piotr J. Chmielewski

2022

Wiley-VCH

Weinheim

583-621

10.1002/9783527834204.ch18

Chiral Building Blocks in Asymmetric Synthesis : Synthesis and Applications

978-3-527-34946-3

Naukowa

Angielski

Rozdział książki

This chapter consists of a presentation of chiral derivatives of 2-aza-21-carbaporphyrin, aka N-confused porphyrin (NCP) that have been reported in the literature since the discovery of this prochiral aromatic macrocycle in 1994. Owing to a special reactivity of the confused pyrrole, majority of these species can be obtained by a post-annulated derivatization of NCP whose synthesis, in turn, is facile, cheap, and effective. Coordination chemistry of NCP is particularly rich and significantly different than that of the regular porphyrins. The metal or metalloid complexes of NCP can be further derivatized owing to the activation of the internal carbon of the confused pyrrole by its coordination as a carbanion. Various types of intrinsic chirality have been recognized for NCP derivatives and their complexes including planar, helical, and topological chiralities. For several systems, enantiomeric resolution and an optical activity have been reported although authors anticipate much higher potential application of the chiral NCP derivatives and their complexes in stereogenic synthesis and catalysis.

https://doi.org/10.1002/9783527834204.ch18