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

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.

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 Creators:
Smith, R. J.1, Author
Trzoss, M.1, Author
Bühl, M.2, Author           
Bienz, S.1, Author
Affiliations:
1Univ Zurich, Inst Organ Chem, Winterthurerstr 190, CH-8057; Zurich, Switzerland;, ou_persistent22              
2Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              

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Free keywords: Cram rule; Felkin-Anh model; diastereoselectivity; ab initio calculations; transition states
 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.

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Language(s): eng - English
 Dates: 2002-08
 Publication Status: Issued
 Pages: -
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 Table of Contents: -
 Rev. Type: Peer
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Title: European Journal of Organic Chemistry
  Alternative Title : Eur. J. Org. Chem.
Source Genre: Journal
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Pages: - Volume / Issue: (16) Sequence Number: - Start / End Page: 2770 - 2775 Identifier: ISSN: 1434-193X