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Single enatiomer free-radical chemistry - Lewis acid-mediated reductions of racemic halides using chiral non-racemic stannanes

Dakternieks, Dainis, Perchyonok, V. Tamara and Schiesser, Carl H. 2003, Single enatiomer free-radical chemistry - Lewis acid-mediated reductions of racemic halides using chiral non-racemic stannanes, Tetrahedron: asymmetry, vol. 14, no. 19, pp. 3057-3068, doi: 10.1016/j.tetasy.2003.07.012.

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Title Single enatiomer free-radical chemistry - Lewis acid-mediated reductions of racemic halides using chiral non-racemic stannanes
Author(s) Dakternieks, Dainis
Perchyonok, V. Tamara
Schiesser, Carl H.
Journal name Tetrahedron: asymmetry
Volume number 14
Issue number 19
Start page 3057
End page 3068
Publisher Elsevier
Place of publication Amsterdam, The Netherlands
Publication date 2003-10-03
ISSN 0957-4166
1362-511X
Summary Additions of one to two equivalents of Lewis acids that include magnesium salts to free-radical reduction reactions involving ester functionalized radicals and (1R,2S,5R)-menthyldiphenyltin hydride 4, bis((1R,2S,5R)-menthyl)phenyltin hydride 5, tris((1R,2S,5R)-menthyl)tin hydride 6, bis((1R,2S,5R)-menthyl)-[8-(N,N-dimethylamino)naphthyl]tin hydride 12, bis((1R,2S,5R)-menthyl)-[1-((S)-N,N-dimethylaminoethyl)phenyl]tin hydride 13 or 3α-dimethylstannyl-5α-cholestane 14 result in remarkable enantioselectivities. Examples include (S)-naproxen ethyl ester 16, produced in 74% yield and greater than 99% ee at −78°C from the bromide and 5 in the presence of MgBr2, and ethyl (R)-N-trifluoroacetyl-D-phenylglycinate 18, obtained in 78% yield and 99% ee under identical conditions. Kinetic and computational studies provide insight into the origins of these observations.


Notes Available online 19 September 2003.
Language eng
DOI 10.1016/j.tetasy.2003.07.012
Field of Research 039904 Organometallic Chemistry
HERDC Research category C1 Refereed article in a scholarly journal
Copyright notice ©2003, Elsevier Ltd.
Persistent URL http://hdl.handle.net/10536/DRO/DU:30001974

Document type: Journal Article
Collection: School of Biological and Chemical Sciences
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