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Enantioselective Co...
Enantioselective Conjugate Silyl Additions to alpha,beta-Unsaturated Aldehydes Catalyzed by Combination of Transition Metal and Chiral Amine Catalysts
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- Ibrahem, Ismail (author)
- Mittuniversitetet,Institutionen för naturvetenskap, teknik och matematik (-2012)
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- Santoro, Stefano (author)
- Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden
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- Himo, Fahmi (author)
- Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden
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- Cordova, Armando (author)
- Mittuniversitetet,Institutionen för naturvetenskap, teknik och matematik (-2012)
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(creator_code:org_t)
- 2011-02-08
- 2011
- English.
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In: Advanced Synthesis and Catalysis. - : Wiley. - 1615-4150 .- 1615-4169. ; 353:2-3, s. 245-252
- 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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- We report that transition metal-catalyzed nucleophilic activation can be combined with chiral amine-catalyzed iminium activation as exemplified by the unprecedented enantioselective conjugate addition of a dimethylsilanyl group to alpha,beta-unsaturated aldehydes. These reactions proceed with excellent 1,4-selectivity to afford the corresponding beta-silyl aldehyde products 3 in high yields and up to 97:3 er using inexpensive bench stable copper salts and simple chiral amine catalysts. The reaction can also generate a quaternary stereocenter with good enantioselectivity. Density functional calculations are performed to elucidate the reaction mechanism and the origin of enantioselectivity.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- asymmetric catalysis; organocatalysis; beta-silyl aldehydes; transition metal catalysis; alpha
- beta-unsaturated aldehydes
- Organic chemistry
- Organisk kemi
Publication and Content Type
- ref (subject category)
- art (subject category)
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