|Title||Computational prediction of the enantioselectivity of a solid-state photoreaction|
|Publication Type||Journal Article|
|Year of Publication||1999|
|Authors||Garcia-Garibay, MA, Houk, KN, Keating, AE, Cheer, CJ, Leibovitch, M, Scheffer, JR, Wu, LC|
|Type of Article||Article|
|Keywords||ABSOLUTE ASYMMETRIC-SYNTHESIS, CRYSTAL LATTICES, FORCE-FIELD, MEDIA, MODEL, MOLECULAR MECHANICS, NUCLEIC-ACIDS, PHOTOCHEMISTRY, PROTEINS|
[GRAPHICS] To better understand the forces controlling chemical reactions in crystals, the absolute asymmetric photorearrangement of 4-m-chlorobenzyloxy-2-pyridone leading to the corresponding enantiomerically enriched (78% ee) beta-lactam was modeled computationally using a flexible minilattice consisting of a central reactant and 20 nearest and 72 next-nearest neighbors. The computational results predicted a preference for formation of the (R,R)-enantiomer, and this was verified experimentally by absolute configuration correlation studies.
|URL||<Go to ISI>://000085172100037|