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  Aldol-additions to α- and β-alkoxy aldehydes: The effect of chelation on simple diastereoselectivity

Reetz, M. T., Kesseler, K., & Jung, A. (1984). Aldol-additions to α- and β-alkoxy aldehydes: The effect of chelation on simple diastereoselectivity. Tetrahedron, 40(21), 4327-4336. doi:10.1016/S0040-4020(01)98807-6.

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Item Permalink: https://hdl.handle.net/21.11116/0000-000E-7FDF-A Version Permalink: https://hdl.handle.net/21.11116/0000-000E-7FE0-7
Genre: Journal Article

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 Creators:
Reetz, M. T.1, Author           
Kesseler, K.1, Author
Jung, A.1, Author
Affiliations:
1Philipps-Universität Marburg, Fachbereich Chemie, Hans-Meerwein-Straße, Marburg, ou_persistent22              

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 Abstract: The TiC14 or SnCl4 mediated reaction of enol silanes with chiral α- and β-alkoxy aldehydes constitutes the only presently known, general way to perform aldol additions with chelation-control (asymmetric induction 90%). If the enol silane is prochiral, the additional stereoselection (simple diastereoselectivity) is surprisingly good. This unusual effect has been traced to syn-type of complexation of the aldehyde function.

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Language(s): eng - English
 Dates: 1984-08-071984
 Publication Status: Issued
 Pages: 10
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/S0040-4020(01)98807-6
 Degree: -

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Title: Tetrahedron
  Abbreviation : Tetrahedron
Source Genre: Journal
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Publ. Info: Kidlington : Elsevier Science
Pages: - Volume / Issue: 40 (21) Sequence Number: - Start / End Page: 4327 - 4336 Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/00404020