Amino Aacohols: stereoselective synthesis and applications in diversity-oriented synthesis
2005 (English)Licentiate thesis, comprehensive summary (Other scientific)
This thesis is divided into three separate parts with amino alcohols as the common feature. The first part describes the development of a novel three-component approach to the synthesis of α-hydroxy-β-amino esters. Utilizing a highly diastereoselective Rh(II)-catalyzed 1,3-dipolar cycloaddition of carbonyl ylides to various aldimines, syn-α-hydroxy-β-amino esters formed in high yields and excellent diastereoselectivities. This methodology was also applied in a short enantioselective synthesis of the C-13 side-chain of Taxol.
The second part of the thesis describes a total synthesis of D-erythro- Sphingosine based on a cross-metathesis approach to assemble the polar head group and the aliphatic chain.
The last part deals with the application of amino alcohols as scaffolds in a diversity-oriented protocol for the development of libraries of small polycyclic molecules. The design of the libraries is based on the iterative use of two powerful ring-forming reactions; a ring-closing metathesis and an intramolecular Diels-Alder reaction, to simultaneously introduce structural complexity and diversity.
Place, publisher, year, edition, pages
Stockholm: KTH , 2005. , 41 p.
Trita-IOK, ISSN 1100-7974 ; 05.95
Organic chemistry, amino alcohol, carbenoid, carbonyl ylide, cross-metathesis, diastereoselective, 1, 3-dipolar cycloaddition, sphingosine
IdentifiersURN: urn:nbn:se:kth:diva-315ISBN: 91-7178-006-8OAI: oai:DiVA.org:kth-315DiVA: diva2:8915
2005-05-09, Sal D41, Lindstedtsvägen 17, Stockholm, 10:00
QC 201012222005-07-182005-07-182010-12-22Bibliographically approved
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