Durand Daniel J, Kondepudi Dilip K, Moreira Paulo F, Quina Frank H
Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109, USA.
Chirality. 2002 May 5;14(4):284-7. doi: 10.1002/chir.10044.
In our earlier work we established that stirred crystallization of achiral compounds that crystallize in enantiomeric forms result in spontaneous chiral symmetry breaking. The asymmetry thus spontaneously generated is confined to the solid state. In this article, we present a case in which the crystal enantiomeric excess (CEE) can be converted to molecular enantiomeric excess (EE) through a solid state reaction which relates the enantiomeric form of the crystal to the enantiomeric form of the product. Such a process not only provides a means of detecting the CEE generated in stirred crystallization but it is also a means through which chiral asymmetry generated spontaneously is "propagated" to generate chiral compounds with enantiomeric excess.
在我们早期的工作中，我们确定了以对映体形式结晶的非手性化合物的搅拌结晶会导致自发的手性对称性破缺。由此自发产生的不对称性局限于固态。在本文中，我们展示了一个案例，其中晶体对映体过量（CEE）可以通过一种固态反应转化为分子对映体过量（EE），该反应将晶体的对映体形式与产物的对映体形式联系起来。这样的过程不仅提供了一种检测搅拌结晶中产生的CEE的方法，而且也是一种将自发产生的手性不对称性“传播”以生成具有对映体过量的手性化合物的方法。
