Diastereoselective photocycloaddition using memory effect of molecular chirality controlled by crystallization.

Asymmetric photocycloaddition of naphthamide with a diene using the provisional molecular chirality in a chiral crystal.

N-(2-Methoxy-1-naphthoyl)piperidine afforded chiral crystals by spontaneous crystallization, and the molecular chirality of the crystals was retained after dissolving them in a cooled solvent. An asymmetric photocycloaddition reaction with a diene was performed using the provisional chiral molecular conformation derived from these chiral crystals.

Asymmetric Reaction Using Molecular Chirality Controlled by Spontaneous Crystallization

Crystallization-induced diastereomer transformation of 2-quinolone-4-carboxamide followed by stereoselective intermolecular photocycloaddition reaction.

2-Quinolone-4-carboxamide derived from (S)-proline, which exists as a mixture of two diastereomers before crystallization, converged to a single diastereomer by crystallization (CIDT), and the homochirality was transferred by a intermolecular 2 + 2 photocycloaddition reaction with high optical activity.

Stereoselective synthesis of the Halaven C14-C26 fragment from D-quinic acid: crystallization-induced diastereoselective transformation of an α-methyl nitrile.

Crystallization-induced diastereoselective transformation (CIDT) of an α-methyl nitrile completes an entirely non-chromatographic synthesis of the halichondrin B C14-C26 stereochemical array. The requisite α-methyl nitrile substrate is derived from D-quinic acid through a series of substrate-controlled stereoselective reactions via a number of crystalline intermediates that benefit from a rigid...

Supramolecular Chirality: Solvent Chirality Transfer in Molecular Chemistry and Polymer Chemistry

Controlled mirror symmetry breaking arising from chemical and physical origin is currently one of the hottest issues in the field of supramolecular chirality. The dynamic twisting abilities of solvent molecules are often ignored and unknown, although the targeted molecules and polymers in a fluid solution are surrounded by solvent molecules. We should pay more attention to the facts that mostly...