Journal article
Allyltrimethoxysilane Addition to N-Acylhydrazones: Two Catalytic Methods Employing CuCl and Fluoride
Synthesis, Vol.2004(13), pp.2216-2221
09/06/2004
DOI: 10.1055/s-2004-829190
Abstract
ABSTRACT Two alternative reaction conditions developed for allyltrimethoxysilane addition to N-benzoylhydrazones enable efficient and versatile access to homoallylic α-branched amines. Aldehyde hydrazones, both aromatic and aliphatic, and ketone hydrazones all give good yields. One set of conditions employs catalytic amounts of CuCl and tetrabutylammonium triphenyldifluorosilicate (TBAT); improved yields and reaction times are obtained at 80 °C in the presence of bis(diphenylphosphino)ethane (dppe) and T-BuOH as additives. The second set of conditions employs 20 mol% TBAT as a fluoride source in a metal-free catalytic system; here T-BuOH offers only modest improvement, and ambient temperatures are optimal. For example, under this second set of conditions, the N-benzoylhydrazone from ethyl pyruvate affords the homoallylic TERT-alkyl amine adduct in 78% yield.
Details
- Title: Subtitle
- Allyltrimethoxysilane Addition to N-Acylhydrazones: Two Catalytic Methods Employing CuCl and Fluoride
- Creators
- Hui DingGregory K Friestad
- Resource Type
- Journal article
- Publication Details
- Synthesis, Vol.2004(13), pp.2216-2221
- DOI
- 10.1055/s-2004-829190
- ISSN
- 0039-7881
- eISSN
- 1437-210X
- Language
- English
- Date published
- 09/06/2004
- Academic Unit
- Chemistry
- Record Identifier
- 9983985886702771
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