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  A rapid injection NMR study of the chelation controlled Mukaiyama aldol addition: TiCl4 versus LiClO4 as the Lewis acid

Reetz, M. T., Raguse, B., Marth, C. F., Hügel, H. M., Bach, T., & Fox, D. N. A. (1992). A rapid injection NMR study of the chelation controlled Mukaiyama aldol addition: TiCl4 versus LiClO4 as the Lewis acid. Tetrahedron, 48(27), 5731-5742. doi:10.1016/0040-4020(92)80024-A.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0023-CA52-7 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0023-CA53-5
Genre: Journal Article

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 Creators:
Reetz, Manfred T.1, 2, Author              
Raguse, Burkhard1, 2, Author
Marth, Charles F.1, 2, Author
Hügel, Helmut M.1, 2, Author
Bach, Thorsten1, 2, Author
Fox, David N. A.1, 2, Author
Affiliations:
1Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445588              
2Fachbereich Chemie der Universität, 3550 Marburg, Germany, ou_persistent22              

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 Abstract: The concept of chelation controlled addition to chiral alkoxy aldehydes using Lewis acids and mild C-nucleophiles has been extended to include cyclopropylation. The mechanism of the TiCl4-mediated chelation controlled addition of enolsilanes and allylsilanes to chiral α-alkoxy aldehydes has been studied by rapid injection NMR techniques. Accordingly, an acyclic transition state is involved in which the silyl group does not migrate to the carbonyl oxygen atom. In contrast, LiClO4 is an effective Lewis acid (excess or catalytic amounts) which induces chelation controlled group transfer type of aldol additions

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Language(s): eng - English
 Dates: 2003-07-171992-07-03
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1016/0040-4020(92)80024-A
 Degree: -

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Title: Tetrahedron
  Other : Tetrahedron
Source Genre: Journal
 Creator(s):
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Publ. Info: Oxford : Pergamon
Pages: - Volume / Issue: 48 (27) Sequence Number: - Start / End Page: 5731 - 5742 Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/954925448773