Diastereo-differentiating hydride transfer at bridged NAD(H) models

A Demonstration of Anion Templation and Selectivity in Pseudorotaxane Formation We thank the EPSRC and the University of Reading for funds for the Image Plate System and the Natural Sciences and Engineering Research Council of Canada for financial support to Dr. Wisner.

“…3,5-Pyridinedicarbonyl chloride was synthesized by a literature procedure [9] from commercially available 3,5-pyridinedicarboxylic acid.…”

Synthesis, X-ray structure and NMR data of 12-amino-15-phenyl-2,5,8-trioxa-13-azabicyclo[9.2.2]pentadeca-1(14),12- diene-11,14-dicarbonitrile

“…The development of new methods which allow the synthesis of [n]pyridinophanes and their dihydro-analogues is a major focus in supramolecular chemistry due to the many roles played by cyclophanes in biology and new technologies. 1 Pyridinophanes and their dihydro-analogues constituted the first examples of NADH models 2,3 capable of mimicking the diastereo-differentiating course of hydride exchange at pyridine dinucleotides under enzymatic conditions. In this way the asymmetric reduction of carbonyl substrates by optically active NADH model compounds has received wide attention.…”

Consideration of molecular arrangements in regio- and enantioselective reduction of an NAD model compound controlled by carbonyl oxygen orientation

“…[27][28][29] Several strategies for the differentiation of the nicotinamide ring face in NAD model compounds have been developed. The C3-C6, 21 C3-C5, 30 or C2-C5 26 strapped NAD model compounds undergo enantiospecific reduction from the unhindered face. Annulation in C2 and C3 results in inclination of the carbamoyl C=O bond from the plane of the nicotinamide ring, mostly activating the syn-face with the carbonyl oxygen in the 1,4reduction.…”