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Development of New ...
Development of New Methodology in Organic Synthesis: Lewis Acid-Mediated Rearrangements of Ammonium Ylides and Addition of 1, 3-bis(silyl) propenes to Aldehydes
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- Tuzina, Pavel, 1980- (författare)
- KTH,Organisk kemi
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- Somfai, Peter, Professor (preses)
- KTH,Organisk kemi
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- Koskinen, Ari, Professor (opponent)
- Helsinki University of Technology
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(creator_code:org_t)
- ISBN 9789174152685
- Stockholm : KTH, 2009
- Engelska 63 s.
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Serie: Trita-CHE-Report, 1654-1081 ; 2009:13
- Relaterad länk:
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https://urn.kb.se/re...
Abstract
Ämnesord
Stäng
- 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.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Nyckelord
- asymmetric
- amino acid
- ammonium ylide
- Lewis acid
- microwave irradiation
- Organic synthesis
- Organisk syntes
Publikations- och innehållstyp
- vet (ämneskategori)
- dok (ämneskategori)
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