The cram rule revisited once more - Revision of the Felkin-Anh model

Smith, R. J.; Trzoss, M.; Bühl, M.; Bienz, S.

doi:10.1002/1099-0690(200208)2002:16<2770::AID-EJOC2770>3.0.CO;2-X

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The cram rule revisited once more - Revision of the Felkin-Anh model

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Bühl, M.
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Smith, R. J., Trzoss, M., Bühl, M., & Bienz, S. (2002). The cram rule revisited once more - Revision of the Felkin-Anh model. European Journal of Organic Chemistry, (16), 2770-2775. doi:10.1002/1099-0690(200208)2002:16<2770:AID-EJOC2770>3.0.CO;2-X.

Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-99B6-3

Abstract

The reaction mechanism of the LiH addition to alpha-chiral ketones and acylsilanes was calculated at the ab initio MP2/6- 311+G (circlecircle)//RHF/6-31G(circle) level. The selectivities predicted on the basis of the computed transition states and reaction barriers compare well with the experimental data, For compounds possessing very large groups, anti-Cram selectivity was found; silicon-containing compounds should show the same types of selectivity as their carbon analogs. The calculations suggest that a revision of the Felkin-Anh model is necessary and a proposal for such a revision is given, (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.