Search: onr:"swepub:oai:DiVA.org:kth-39526" >
Diastereoselective ...
Diastereoselective Nucleophilic Addition to Aldehydes with Polar alpha- and alpha,beta-Substituents
-
- Borg, Tessie (author)
- KTH,Organisk kemi,Peter Somfai
-
- Danielsson, Jakob (author)
- KTH,Organisk kemi,Peter Somfai
-
- Mohiti, Maziar (author)
- KTH,Organisk kemi
-
show more...
-
- Restorp, Per (author)
- KTH,Organisk kemi
-
- Somfai, Peter (author)
- KTH,Organisk kemi
-
show less...
-
(creator_code:org_t)
- 2011-08-10
- 2011
- English.
-
In: Advanced Synthesis and Catalysis. - : Wiley. - 1615-4150 .- 1615-4169. ; 353:11-12, s. 2022-2036
- Related links:
-
https://urn.kb.se/re...
-
show more...
-
https://doi.org/10.1...
-
show less...
Abstract
Subject headings
Close
- 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.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Keyword
- aldol reaction
- allylation
- diastereoselectivity
- induction model
Publication and Content Type
- ref (subject category)
- art (subject category)
Find in a library
To the university's database