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The cram rule revisited once more — revision of the Felkin−Anh Model


Smith, Richard J; Trzoss, Michael; Bühl, Michael; Bienz, Stefan (2002). The cram rule revisited once more — revision of the Felkin−Anh Model. European Journal of Organic Chemistry, 2002(16):2770-2775.

Abstract

The reaction mechanism of the LiH addition to α-chiral ketones and acylsilanes was calculated at the ab initio MP2/6-311+G**//RHF/6-31G* 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

Abstract

The reaction mechanism of the LiH addition to α-chiral ketones and acylsilanes was calculated at the ab initio MP2/6-311+G**//RHF/6-31G* 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

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:24 July 2002
Deposited On:23 Aug 2017 15:57
Last Modified:09 Dec 2017 01:52
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:1099-0690
Publisher DOI:https://doi.org/10.1002/1099-0690(200208)2002:16<2770::AID-EJOC2770>3.0.CO;2-X

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