WFRF:(Somfai Peter)
Sökning: WFRF:(Somfai Peter) > Asymmetric [2,3]-Si...
LIBRIS Formathandbok (Information om MARC21)
| Fältnamn | Indikatorer | Metadata |
|---|---|---|
| 000 | 03126nam a2200481 4500 | |
| 001 | oai:DiVA.org:kth-430 | |
| 003 | SwePub | |
| 008 | 050927s2005 | |||||||||||000 ||eng| | |
| 020 | a 9171781358q print | |
| 024 | 7 | a https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-4302 URI |
| 040 | a (SwePub)kth | |
| 041 | a engb eng | |
| 042 | 9 SwePub | |
| 072 | 7 | a vet2 swepub-contenttype |
| 072 | 7 | a dok2 swepub-publicationtype |
| 100 | 1 | a Blid, Jan,d 1970-u KTH,Organisk kemi4 aut0 (Swepub:kth)u1r6n23d |
| 245 | 1 0 | a Asymmetric [2,3]-Sigmatropic Rearrangement of Allylic Ammonium Ylides |
| 264 | 1 | a Stockholm :b KTH,c 2005 |
| 300 | a 68 s. | |
| 338 | a electronic2 rdacarrier | |
| 490 | 0 | a Trita-IOK,x 1100-7974 ;v 2005:97 |
| 500 | a QC 20100927 | |
| 520 | a The thesis describes the realization of an asymmetric [2,3]-sigmatropic rearrangement of achiral allylic amines. It is divided into two parts; the first part deals with the development of a Lewis acid-mediated [2,3]-sigmatropic rearrangement and the second the asymmetric version thereof. Quaternization of an -amino amide with various Lewis acids established BBr3 and BF3 to be the most appropriate ones. Various allylic amines were subsequently rearranged into the corresponding homoallylic amines in good to excellent syn-diastereoselectivities, revealing the endo-transition state to be the preferred pathway. The structures of the intermediate Lewis acid-amine complexes were confirmed by NMR spectroscopy studies and DFT calculations. Based on this investigation a chiral diazaborolidine was chosen as Lewis acid and was shown to efficiently promote the asymmetric [2,3]-sigmatropic rearrangement furnishing homoallylic amines in good yields and excellent enantiomeric excesses. In contrast to the achiral rearrangement mediated by BBr3 and BF3, the asymmetric version gave the opposite major diastereomer, revealing a preference for the exo-transition state in the asymmetric rearrangement. To account for the observed selectivities, a kinetic and thermodynamic pathway was presented. On the basis of a deuterium exchange experiment on a rearranged Lewis acid-amine complex and an NMR spectroscopic investigation, the kinetic pathway was shown to be favored. | |
| 650 | 7 | a NATURVETENSKAPx Kemix Organisk kemi0 (SwePub)104052 hsv//swe |
| 650 | 7 | a NATURAL SCIENCESx Chemical Sciencesx Organic Chemistry0 (SwePub)104052 hsv//eng |
| 653 | a asymmetric | |
| 653 | a [2 | |
| 653 | a 3]-sigmatropic rearrangement | |
| 653 | a allylic amine | |
| 653 | a ammonium ylide | |
| 653 | a Lewis acid | |
| 653 | a enantioselective | |
| 653 | a boron | |
| 653 | a phosphazene base | |
| 653 | a NMR spectroscopy | |
| 653 | a DFT-calculations | |
| 653 | a Organic chemistry | |
| 653 | a Organisk kemi | |
| 700 | 1 | a Somfai, Peteru KTH,Organisk kemi4 ths |
| 700 | 1 | a Anderson, James C.u Chemistry4 opn |
| 710 | 2 | a KTHb Organisk kemi4 org |
| 856 | 4 | u https://kth.diva-portal.org/smash/get/diva2:11708/FULLTEXT01.pdfx primaryx Raw objecty fulltext |
| 856 | 4 8 | u https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-430 |
Hitta via bibliotek
- Asymmetric [2,3]-Sigmatropic Rearrangement of Allylic Ammonium Ylides (Sök publikationen i LIBRIS)
Till lärosätets databas
Hitta mer i SwePub
- Av författaren/redakt...
- Blid, Jan, 1970-
- Somfai, Peter
- Anderson, James ...
- Om ämnet
-
- NATURVETENSKAP
- NATURVETENSKAP
- och Kemi
- och Organisk kemi
- Delar i serien
- Trita-IOK,
- Av lärosätet
- Kungliga Tekniska Högskolan
Sök utanför SwePub
- Sök vidare i:
- Google Book Search
- Google Scholar
Kungliga biblioteket hanterar dina personuppgifter i enlighet med EU:s dataskyddsförordning (2018), GDPR. Läs mer om hur det funkar här.
Så här hanterar KB dina uppgifter vid användning av denna tjänst.
- Copyright © LIBRIS - Nationella bibliotekssystem
- LIBRIS.kb.se
