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Asymmetric Lewis Acid Mediated 1,2 -Rearrangement of Proline-Derived Ammonium Ylides
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: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 4, 919-921 p.Article in journal (Refereed) Published
Abstract [en]

The first example of asymmetric Lewis acid mediated [1,2]-rearrangement of N-benzylic proline amides to form quaternary proline derivatives is reported. The presented reaction is shown to proceed with remarkable high C-N-C chirality transfer. Various quaternary proline derivatives have been prepared in good to excellent yields and high enantiomeric purity.

Place, publisher, year, edition, pages
2009. Vol. 11, no 4, 919-921 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-18170DOI: 10.1021/ol8028803ISI: 000263299000034Scopus ID: 2-s2.0-62749167066OAI: oai:DiVA.org:kth-18170DiVA: diva2:336216
Note
QC 20100525Available from: 2010-08-05 Created: 2010-08-05 Last updated: 2017-12-12Bibliographically approved
In thesis
1. Development of New Methodology in Organic Synthesis: Lewis Acid-Mediated Rearrangements of Ammonium Ylides and Addition of 1, 3-bis(silyl) propenes to Aldehydes
Open this publication in new window or tab >>Development of New Methodology in Organic Synthesis: Lewis Acid-Mediated Rearrangements of Ammonium Ylides and Addition of 1, 3-bis(silyl) propenes to Aldehydes
2009 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis deals with the development of new methodologies in organicsynthesis. The main focus is on the development of Lewis acid-mediated [1,2]-rearrangements of ammonium ylides and the novel addition of 1,3-bis(silyl)propenes to carbonyl compounds.The first part of this thesis describes the development of a Lewis acidmediated[1,2]-Stevens rearrangement of various glycine derivatives. Thismethodology was then applied to the development of an asymmetric Lewis acid mediated [1,2]-Stevens rearrangement of cyclic ammonium ylides. There markably high degree of C→N→C chirality transfer is described. In addition, this methodology was successfully applied to the synthesis of various quaternary proline derivatives in enantiomerically pure form.Secondly, a brief study of the asymmetric [2,3]-rearrangement of α-substitutedglycine derivatives is presented. The investigation revealed a severely limitedreaction scope. The subsequent study on developing super-reactive cationicLewis acid also met with little success.Finally, an addition reaction of various 1,3-bis(silyl)propenes to glyoxalates has been developed. The reaction products correspond to the direct vinylation ofglyoxalates. The corresponding highly functionalized δ-hydroxy allylsilanes were obtained in high yields.

Place, publisher, year, edition, pages
Stockholm: KTH, 2009. 63 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2009:13
Keyword
asymmetric, amino acid, ammonium ylide, Lewis acid, microwave irradiation
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-10317 (URN)978-91-7415-268-5 (ISBN)
Public defence
2009-04-24, F3. KTH, Lindstedtsvägen 26, Stockholm, 13:00 (English)
Opponent
Supervisors
Note
QC 20100812Available from: 2009-05-06 Created: 2009-05-06 Last updated: 2010-08-12Bibliographically approved

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