New Methodologies in Organic Chemistry: Applications to the Synthesis of α-Amino Acids and Natural Products
2009 (English)Doctoral thesis, comprehensive summary (Other academic)
This thesis deals with the development and application of new synthetic methodology in organic chemistry.
The first part describes the development of a new protocol for the synthesis of 3-pyrrolines by means of a microwave-assisted ring-expansion reaction of 2-vinylaziridines. In addition, this methodology is implemented as a key-step in a formal total synthesis of the antibiotic (-)-anisomycin.
In the second part, a new methodology for the synthesis of arylglycines from Weinreb amides is described. In this procedure, a Grignard reagent is added to the iminium ion formed from the Weinreb amide upon treatment with a base. When a chiral amide is used, the nucleophilic addition proceeds with high diastereoselectivity.
Finally, an easy and straightforward synthesis of α-amino amides via a base-mediated rearrangement of modified Weinreb amides into N,O-acetals is presented. Subsequent arylation, alkylation, alkenylation or alkynylation of this intermediate affords the corresponding α-amino amides in excellent yields. Furthermore, a more generalized protocol for the α-arylation of Weinreb amides lacking an α-amino moiety is also discussed.
Place, publisher, year, edition, pages
Stockholm: Kemi , 2009. , 64 p.
Trita-CHE-Report, ISSN 1654-1081 ; 2009:46
Organic synthesis, 2-Vinylaziridines, 3-Pyrrolines, Ringexpansion, Rearrangement, Anisomycin, Total synthesis, α-Amino acids, Arylglycines, Weinreb amides, α-Arylation, Grignard reagents, Umpolung
IdentifiersURN: urn:nbn:se:kth:diva-11112ISBN: 978-91-7415-404-7OAI: oai:DiVA.org:kth-11112DiVA: diva2:236033
2009-10-09, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (English)
Aggarwal, Varinder, Professor
Somfai, Peter, Professor
QC 201007192009-09-222009-09-202011-09-06Bibliographically approved
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