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Highly stereoselective alkylation of (S)-proline-based chiral auxiliaries
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.ORCID iD: 0000-0002-5543-2041
Responsible organisation
2004 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 15, no 16, 2539-2545 p.Article in journal (Refereed) Published
Abstract [en]

Alkylation of the enolates of the propanoylamides of two chiral auxiliaries (S)-(-)-2-(pyrrolidin-2-yl)propan-2-ol 1a and (S)-(-)-2-(2-methoxypropan-2-yl)pyrrolidine 1b, derived from (S)-proline, with benzyl bromide and n-butyl iodide has been studied. The auxiliaries 1a and 1b induced opposite selectivity that is (R)- and (S)-configuration, respectively, at the newly created stereogenic centre. The diastereoselectivities and conversion yields in these alkylations were moderate to excellent. When Cp2ZrCl2 was used as an enolate coordinating agent, benzylation of propanoylated 1b gave an excellent diastereomeric ratio of 99:1. The benzylated diastereomeric products from either propanoylated 1a or 1b were easily separated by liquid chromatography.

Place, publisher, year, edition, pages
2004. Vol. 15, no 16, 2539-2545 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-2416DOI: 10.1016/j.tetasy.2004.06.045ISI: 000223666600013Local ID: 2394OAI: oai:DiVA.org:miun-2416DiVA: diva2:27448
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-09-29Bibliographically approved

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Andersson, FredrikHedenström, Erik
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