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Synthesis of alpha-Amino Acids by Umpolung of Weinreb Amide Enolates
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2008 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 33, 5583-5589 p.Article in journal (Refereed) Published
Abstract [en]

An efficient and diastereoselective synthesis of alpha-amino acids from readily available starting materials has been developed. The key feature of this reaction is an umpolung of a glycine-derived enolate, providing an alternative approach for the synthesis of alpha-amino acids.

Place, publisher, year, edition, pages
2008. no 33, 5583-5589 p.
Keyword [en]
Amino acids, Umpolung, Arylglycines, Grignard reaction, Weinreb amides
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-11128DOI: 10.1002/ejoc.200800683ISI: 000261553700011Scopus ID: 2-s2.0-56049091042OAI: oai:DiVA.org:kth-11128DiVA: diva2:236250
Funder
Swedish Research CouncilKnut and Alice Wallenberg Foundation
Note
QC 20100719Available from: 2009-09-22 Created: 2009-09-22 Last updated: 2017-12-13Bibliographically approved
In thesis
1. New Methodologies in Organic Chemistry: Applications to the Synthesis of α-Amino Acids and Natural Products
Open this publication in new window or tab >>New Methodologies in Organic Chemistry: Applications to the Synthesis of α-Amino Acids and Natural Products
2009 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

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.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2009:46
Keyword
Organic synthesis, 2-Vinylaziridines, 3-Pyrrolines, Ringexpansion, Rearrangement, Anisomycin, Total synthesis, α-Amino acids, Arylglycines, Weinreb amides, α-Arylation, Grignard reagents, Umpolung
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-11112 (URN)978-91-7415-404-7 (ISBN)
Public defence
2009-10-09, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
QC 20100719Available from: 2009-09-22 Created: 2009-09-20 Last updated: 2011-09-06Bibliographically approved

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