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Diastereoselective ...
Diastereoselective Nucleophilic Addition to Aldehydes with Polar alpha- and alpha,beta-Substituents
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- Borg, Tessie (författare)
- KTH,Organisk kemi,Peter Somfai
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- Danielsson, Jakob (författare)
- KTH,Organisk kemi,Peter Somfai
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- Mohiti, Maziar (författare)
- KTH,Organisk kemi
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- Restorp, Per (författare)
- KTH,Organisk kemi
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- Somfai, Peter (författare)
- KTH,Organisk kemi
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(creator_code:org_t)
- 2011-08-10
- 2011
- Engelska.
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Ingår i: Advanced Synthesis and Catalysis. - : Wiley. - 1615-4150 .- 1615-4169. ; 353:11-12, s. 2022-2036
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- The stereoselectivities obtained in Lewis acid-promoted Mukaiyama aldol additions and Sakurai allylations of mono-, and syn- and anti-disubstituted aldehydes possessing various polar alpha- and beta-substituents under non-chelating conditions are presented. The stereochemical outcome in the nucleophilic addition to alpha-substituted aldehydes containing an alpha-benzyloxy, alpha-fluoro or alpha-sulfonamide substituent are accurately predicted by current stereoinduction models. In contrast, the selectivitites obtained from addition of sterically demanding nucleophiles to alpha-chloro-substituted aldehydes cannot be rationalized by the same models and an alternative is discussed. The stereochemichal outcome in the additions to alpha, beta-disubstituted aldehydes is more complex and cannot be predicted using current models.
Ämnesord
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Nyckelord
- aldol reaction
- allylation
- diastereoselectivity
- induction model
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
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