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Rhodium-catalysed c...
Rhodium-catalysed coupling of allylic, homoallylic, and bishomoallylic alcohols with aldehydes and N-tosylimines : insights into the mechanism
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- Ahlsten, Nanna, 1982- (author)
- Stockholms universitet,Institutionen för organisk kemi
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- Martín-Matute, Belén (author)
- Stockholms universitet,Institutionen för organisk kemi
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(creator_code:org_t)
- 2009-10-21
- 2009
- English.
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In: Advanced Synthesis and Catalysis. - : Wiley. - 1615-4150 .- 1615-4169. ; 351:16, s. 2657-2666
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- The isomerisation of alkenols followed by reaction with aldehydes or N-tosylimines catalysed by rhodium complexes has been studied. The catalytically active rhodium complex is formed in situ from commercially available (cyclooctadiene)rhodium(l) chloride dimer [Rh(COD)Cl](2). The tandem process affords aldol and Mannich-type products in excellent yields. The key to the success of the coupling reaction is the activation of the catalysts by reaction with postassium tert-butoxide (t-BuOK), which promotes a catalytic cycle via alkoxides rather than rhodium hydrides. This mechanism minimises the formation of unwanted by-products. The mechanism has been studied by (1)H NMR spectroscopy and deuterium labelling experiments.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- aldehydes
- allylic alcohols
- isomerization
- rhodium
- N-tosylmines
- Organic chemistry
- Organisk kemi
- organisk kemi
- Organic Chemistry
Publication and Content Type
- ref (subject category)
- art (subject category)
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