H. Koshima, K. Ding, Y. Chisaka
Dec 4, 1996
Citations
0
Influential Citations
64
Citations
Journal
Journal of the American Chemical Society
Abstract
Despite the fact that acridine (1) and diphenylacetic acid (a) are achiral compounds, a chiral two-component molecular crystal (1·a) in which two molecules are self-assembled in a 1:1 molar ratio by hydrogen bonding crystallizes spontaneously from an acetonitrile solution. The space group is P212121, which is typical chiral space group. Both handed crystals (−)-1·a and (+)-1·a can be prepared as desired on a large scale by seeding. The two phenyl planes and the carboxyl plane of the diphenylacetic acid molecule in the crystal (−)-1·a have torsions in the same direction as the blades of a propeller. The oppositely handed crystal (+)-1·a has minus torsion angles. Irradiation of (−)-1·a or (+)-1·a caused stereospecific decarboxylating condensation to give an excess of the chiral compound {(−)-3} or {(+)-3} in about 35% ee, respectively, as the main product. The absolute configurations of the reactant (−)-1·a and the product (−)-3 could be determined to be (M)-(−)-1·a and (S)-(−)-3 by the Bijvoet method based...