uu.seUppsala University Publications
Change search
ReferencesLink to record
Permanent link

Direct link
Fast Chemistry by Microwave Heating: First Descriptions of Highly Enantioselective Microwave Protocols for Metal Catalysis; First Descriptions of in-situ Gas Generation for Fast Combinatorial Microwave Chemistry
Uppsala University, Medicinska vetenskapsområdet, Faculty of Pharmacy, Department of Medicinal Chemistry.
2001 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Microwave heating was applied to different palladium-catalyzed allylic substitution reactions. The use of various nucleophiles demonstrated C-, N-, O- and S- nucleophilicity. High yields and stereopurities of the corresponding alkyls, amides, ethers and sulfones were afforded after only 30 – 120 s of heating. The sensitive stereocontrol induced by the catalyst and the catalytic activity were sustained (88 to > 99 % enantiomeric excess (ee) ) despite high temperatures (up to 215oC) and forced conditions.

Rapid molybdenum-catalyzed allylic alkylation was undertaken utilizing microwave heating. This formerly troublesome catalysis was developed into a simple, fast and convenient protocol. The protocol was employed in a structure-activity investigation for optimizing catalytic activity. An electron-rich environment with low steric restriction around the catalyzing molybdenum improved catalytic activity as well as induced stereoselectivity (> 99 % ee).

A new methodology was developed for performing carbon monoxide reactions without the use of gaseous carbon monoxide from an external source. Solid metal carbonyls of low toxicity were utilized for in situ liberation of carbon monoxide directly into the reaction mixture. The methodology was applied to the combinatorial microwave-assisted synthesis of a small sized substance library of amidated HIV-1 protease inhibitors.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis , 2001. , 65 p.
Comprehensive Summaries of Uppsala Dissertations from the Faculty of Pharmacy, ISSN 0282-7484 ; 254
Keyword [en]
Pharmaceutical chemistry
Keyword [sv]
Farmaceutisk kemi
National Category
Medicinal Chemistry
Research subject
Organic Pharmaceutical Chemistry
URN: urn:nbn:se:uu:diva-1391ISBN: 91-554-5073-3OAI: oai:DiVA.org:uu-1391DiVA: diva2:160891
Public defence
2001-10-05, sal B42, BMC, Uppsala, 10:00
Available from: 2001-10-03 Created: 2001-10-03Bibliographically approved

Open Access in DiVA

No full text
Buy this publication >>

By organisation
Department of Medicinal Chemistry
Medicinal Chemistry

Search outside of DiVA

GoogleGoogle Scholar

Total: 213 hits
ReferencesLink to record
Permanent link

Direct link