Computational Prediction of the Enantioselectivity of a Solid-State Photoreaction

Computational Prediction of the Enantioselectivity of a Solid-State Photoreaction

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) β-lactam was modeled computationally using a flexible minilattice consisting of a c...

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Veröffentlicht in:Organic letters 1999-10, Vol.1 (8), p.1279-1281
Hauptverfasser: Garcia-Garibay, Miguel A, Houk, K. N, Keating, Amy E, Cheer, Clair J, Leibovitch, Mordechai, Scheffer, John R, Wu, Lian-Chung
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container_end_page 1281
container_issue 8
container_start_page 1279
container_title Organic letters
container_volume 1
creator Garcia-Garibay, Miguel A
Houk, K. N
Keating, Amy E
Cheer, Clair J
Leibovitch, Mordechai
Scheffer, John R
Wu, Lian-Chung
description 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) β-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.
doi_str_mv 10.1021/ol990952d
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title Computational Prediction of the Enantioselectivity of a Solid-State Photoreaction
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