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1,3-Dipolar Cycloaddition of Azomethine Ylides to Aldehydes: Synthesis of anti alpha-Amino-beta-Hydroxy Esters
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. (Peter Somfai)
Institute of Technology, University of Tartu, Tartu, Estonia.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2011 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 3, 607-613 p.Article in journal (Refereed) Published
Abstract [en]

A 1,3-dipolar cycloaddition reaction of azomethine ylides to aldehydes is described. The azomethine ylides, generated by thermal electrocyclic ring opening of aziridines, adds to aldehydes in good yields with moderate to good selectivities to furnish oxazolidines. The oxazolidines were subsequently hydrolyzed to the corresponding amino alcohols, giving the anti diastereomer as the major product.

Place, publisher, year, edition, pages
2011. no 3, 607-613 p.
Keyword [en]
Cycloaddition, Azomethine ylides, Aldehydes, Amino alcohols
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-30958DOI: 10.1002/ejoc.201001274ISI: 000287162700019Scopus ID: 2-s2.0-78651330597OAI: oai:DiVA.org:kth-30958DiVA: diva2:402243
Funder
Knut and Alice Wallenberg FoundationSwedish Research Council
Note
QC 20110307Available from: 2011-03-07 Created: 2011-03-07 Last updated: 2012-06-11Bibliographically approved
In thesis
1. Stereoselective Nucleophilic Additions to Aldehydes and Synthesis of α-Amino-β- Hydroxy-Esters
Open this publication in new window or tab >>Stereoselective Nucleophilic Additions to Aldehydes and Synthesis of α-Amino-β- Hydroxy-Esters
2012 (English)Licentiate thesis, comprehensive summary (Other academic)
Abstract [en]

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.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2012:32
Keyword
Asymmetric induction, stereochemical models, Mukaiyama, polar Felkin-Anh, Cornforth-Evans, 1, 3-dipole, aziridine, cycloaddition, amino alcohol, carbonylation, Heck reaction, quaternary stereocenter
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-95467 (URN)978-91-7501-396-1 (ISBN)
Presentation
2012-08-16, F3, KTH, Lindstedtsvägen 3, entréplan, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
QC 20120611Available from: 2012-06-11 Created: 2012-05-25 Last updated: 2012-06-12Bibliographically approved

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