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Synthesis of alpha-Amino Amides via N,O-Acetals Derived from Weinreb Amides
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2009 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 74, no 20, 7798-7803 p.Article in journal (Refereed) Published
Abstract [en]

An easy and straightforward synthesis of alpha-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 alpha-amino amides in excellent yields. Furthermore, a more generalized protocol for the alpha-arylation of Weinreb amides lacking an alpha-amino moiety is also discussed.

Place, publisher, year, edition, pages
2009. Vol. 74, no 20, 7798-7803 p.
Keyword [en]
phase-transfer catalysis; acid-derivatives; enantioselective synthesis; asymmetric-synthesis; efficient synthesis; imino esters; rearrangement; clopidogrel; peptides; glycines
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-14142DOI: 10.1021/jo9015166ISI: 000270504900025Scopus ID: 2-s2.0-70349871066OAI: oai:DiVA.org:kth-14142DiVA: diva2:330699
Note
QC 20100719Available from: 2010-07-19 Created: 2010-07-19 Last updated: 2017-12-12Bibliographically 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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