Stereoselective Nucleophilic Additions to Aldehydes and Synthesis of α-Amino-β- Hydroxy-Esters
2012 (English)Licentiate thesis, comprehensive summary (Other academic)
This thesis deals with the development of new reaction methodology as well as stereochemical investigations.
The first part concerns the investigation of 1,2- and merged 1,2- and 1,3- asymmetric induction in Mukaiyama aldol additions to α-heteroatom and α,β- heteroatom substituted aldehydes respectively. In particular, the unexpected 1,2-syn selectivity obtained in the addition of sterically hindered nucleophiles to α-chloroaldehydes is examined, and an explanation for the observed stereochemical trends is proposed.
The second part describes the development of a novel entry to α-amino-β- hydroxy esters by a 1,3-dipolar cycloaddition reaction of aldehydes and azomethine ylides, generated by thermolysis of aziridines.
The third part deals with our efforts to develop a novel entry to vicinal all- carbon quaternary centers, based on an intramolecular domino Heck- carbonylation reaction using tetrasubstituted olefins.
Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2012. , 60 p.
Trita-CHE-Report, ISSN 1654-1081 ; 2012:32
Asymmetric induction, stereochemical models, Mukaiyama, polar Felkin-Anh, Cornforth-Evans, 1, 3-dipole, aziridine, cycloaddition, amino alcohol, carbonylation, Heck reaction, quaternary stereocenter
IdentifiersURN: urn:nbn:se:kth:diva-95467ISBN: 978-91-7501-396-1OAI: oai:DiVA.org:kth-95467DiVA: diva2:528536
2012-08-16, F3, KTH, Lindstedtsvägen 3, entréplan, Stockholm, 10:00 (English)
Adolfsson, Hans, ProfessorRein, Tobias, Dr
Somfai, Peter, Professor
QC 201206112012-06-112012-05-252012-06-12Bibliographically approved
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