Two-step asymmetric reaction using the frozen chirality generated by spontaneous crystallization.

Org Lett

Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.

Published: May 2012

AI Article Synopsis

  • The compound N,N-diallyl-4-methyl-1-propyl-2-quinolone-3-carboxamide formed chiral crystals in a P2(1) crystal system through spontaneous crystallization.
  • The molecular chirality in these crystals remained intact even after dissolution in a cold solvent.
  • This preserved chirality was successfully transferred to new products via a two-step reaction involving hydrogenation followed by intermolecular photocycloaddition.

Article Abstract

N,N-diallyl-4-methyl-1-propyl-2-quinolone-3-carboxamide afforded chiral crystals of a P2(1) crystal system by spontaneous crystallization. The molecular chirality in the crystal was retained after the crystals were dissolved in a solvent at a low temperature, and the frozen molecular chirality was effectively transferred to the products by a two-step reaction involving hydrogenation and intermolecular photocycloaddition reactions.

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Source
http://dx.doi.org/10.1021/ol301033rDOI Listing

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