Bispyridylamides as ligands in asymmetric catalysis | Belda de Lama Oscar 1976- , KTH, Kemi

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Bispyridylamides as ligands in asymmetric catalysis

Title: Trita-IOK

Description:

This thesis deals with the preparation and use of chiralbispyridylamides as ligands in metal-catalyzed asymmetricreactions.

The compounds were prepared by amide formation usingdifferent coupling reagents. Bispyridylamides havingsubstituents in the 4- or 6- positions of the pyridine ringswere prepared by functional group interconversion of the 4- or6- halopyridine derivatives. These synthetic approaches provedto be useful for various types of chiral backbones. Pseudo C₂-symmetric bispyridylamides were also synthesizedby means of stepwise amide formation.

The compounds were used as ligands in themicrowave-accelerated Mocatalyzed asymmetric allylic alkylationreaction. Ligands having ð-donating substituents in the4-positions of the pyridine rings gave rise to products withhigher branched to linear ratio. The catalytic reaction, whichproved to be rather general for allylic carbonates with anaromatic substituent, was used as the key step in thepreparation of (R)-baclofen. The Mo-bispyridylamide catalystprecursor was studied by NMR spectroscopy.

Bispyridylamide complexes of metal alkoxides were alsoevaluated in the asymmetric addition of cyanide to aldehydesand the metal complexes involved were studied by NMRspectroscopy and X-ray crystallography. Chiral diamines wereused as additives to study the ring opening of cyclohexeneoxide with azide, catalyzed by Zr(IV)-bispyridylamidecomplexes.

Various bispyridylamides were attached to solid supports oforganic or inorganic nature. The solid-supported ligands wereused in Mo-catalyzed asymmetric allylic alkylation reactionsand in the asymmetric addition of cyanide to benzaldehyde.

Keywords:asymmetric catalysis, chiral ligand, pyridine,amide, allylic alkylation, enantioselective, cyanation,ring-opening, chiral Lewis acid.

; Diss. (sammanfattning) Stockholm : Kungliga Tekniska högskolan, 2004

Creator:

Belda de Lama Oscar 1976- , KTH, Kemi

Contributor: KTH Tidigare Institutioner Kemi

Date: 2004; 2004-05-28T00:00:00; 2004-05-27T00:00:00; http://semium.org/time/2004

Type: science; vet; Other scientific; Övrigt vetenskapligt; Annet vitenskapelig; comprehensiveDoctoralThesis; dok; Doctoral thesis, comprehensive summary; Doktorsavhandling, sammanläggning; Doktoravhandling, med artikler; dissertation; text; http://www.eionet.europa.eu/gemet/concept/7472; http://www.eionet.europa.eu/gemet/concept/13026

Format: electronic61; electronic; 61

Identifier: 91-7283-724-1; url: http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-3764; 1100-7974; 2004:88

Relation: Trita-IOK1100-79742004:88

Language: eng

Publisher: Kemi

Data provider: Uppsala Universitet

Provider: The European Library

Providing country: Sweden

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