On the Origin of π-Facial Diastereoselectivity in Addition Reactions of 
Cyclohexane-Based Systems

Frenking, Gernot; Köhler, Klaus F.; Reetz, Manfred T.

doi:10.1002/anie.199111461

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

On the Origin of π-Facial Diastereoselectivity in Addition Reactions of Cyclohexane-Based Systems

MPS-Authors

There are no MPG-Authors in the publication available

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

Citation

Frenking, G., Köhler, K. F., & Reetz, M. T. (1991). On the Origin of π-Facial Diastereoselectivity in Addition Reactions of Cyclohexane-Based Systems. Angewandte Chemie, International Edition in English, 30(9), 1146-1149. doi:10.1002/anie.199111461.

Cite as: https://hdl.handle.net/21.11116/0000-000E-7CD3-9

Abstract

The unsymmetric electron density distribution of the LUMOs of the carbonyl π-bond of cyclohexanones (in the picture C is left, O right) is the reason for preferred axial attack (a) of these compounds by nucleophiles. If the ketones are substituted in the 3-position by electronegative substituents (e.g. halogens), this tendency is enhanced still further. The authors have been able to demonstrate this by quantum mechanical ab-initio calculations.