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Direct catalytic asymmetric three-component Mannich reactions with dihydroxyacetone: enantioselective synthesis of amino sugar derivatives
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2008 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1873-3581, Vol. 49, no 5, 803-807 p.Article in journal (Refereed) Published
Abstract [en]

Highly enantioselective, amino acid-catalyzed, one-pot three-component asymmetric Mannich reactions between dihydroxyacetone, p-anisidine, and aldehydes are presented. The reactions proceeded with high chemo- and stereoselectivity and furnished the corresponding α,α′-dihydroxy-β-aminoketones in high yields with 82–95% ee.

Place, publisher, year, edition, pages
2008. Vol. 49, no 5, 803-807 p.
Identifiers
URN: urn:nbn:se:su:diva-13153DOI: 10.1016/j.tetlet.2007.11.196ISI: 000253170200014OAI: oai:DiVA.org:su-13153DiVA: diva2:179673
Available from: 2008-12-03 Created: 2008-12-03 Last updated: 2010-05-12Bibliographically approved
In thesis
1. Amino acid-catalyzed synthesis of amino acid derivatives: Application and semi-synthesis of Paclitaxel, Docetaxel and their derivatives
Open this publication in new window or tab >>Amino acid-catalyzed synthesis of amino acid derivatives: Application and semi-synthesis of Paclitaxel, Docetaxel and their derivatives
2010 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis deals with different applications of organocatalysis, where amino acid derivatives and small peptides are applied as catalysts. First, the development of environmentally friendly aldol reactions, carried out in aqueous media is illustrated. The corresponding β-hydroxy ketones are formed with ee´s up to 99%. Chapter 3 describes the ability of β3-amino acids to selectively catalyze Mannich-type reactions and govern the formation of products with high anti-selectivity (up to >19:1) and ee´s up to 99%. In the following chapter, an amino acid-catalyzed one-pot three component Mannich reaction between dihydroxyacetone and PMP-protected imines, is presented. The corresponding a,a’-dihydroxy-b-aminoketones are obtained in high yields and with 82-95% ee. Next, an aza-Morita-Baylis-Hillman reaction was investigated where L-proline is the catalyst. The reaction proceeds with excellent chemo- and enantioselectivity to give the corresponding compounds in good yields and with 97-99% ee. Finally, the last part describes development of a proline-catalyzed Mannich reation between N-acyl imines and protected α-hydroxyaldehyes, providing access to different α-hydroxy-β-amino acids in good yields and high enantioselctivity (92-99% ee). The obtained amino acids were further applied in the semisynthesis of paclitaxel and docetaxel derivatives.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2010. 73 p.
Keyword
Organocatlysis, amino acids, syntesis, Taxol and Taxotere derivatives
National Category
Other Basic Medicine
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-39138 (URN)978-91-7447-091-8 (ISBN)
Public defence
2010-06-11, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16b, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 7: Manuscript.Available from: 2010-05-20 Created: 2010-05-10 Last updated: 2010-05-12Bibliographically approved

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