Journal
TETRAHEDRON-ASYMMETRY
Volume 20, Issue 13, Pages 1561-1567Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2009.06.001
Keywords
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Funding
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft
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A copper-catalyzed conjugate addition of Grignard reagents to 1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-1-alkenes led to 1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-2-branched alkanes. Various copper ligands were screened for this reaction. From certain substrates and allylmagnesium bromide, several Josiphos ligands gave low to moderate asymmetric inductions, along with good diastereoselectivity. The stereochemistry of the 1-(N,N-diisopropylcarbamoyloxy)-1-tosyl-2-branched alkanes from this reaction was assigned by comparison with the same products from another synthetic route using chiral pool synthesis and stereoselective lithiation methods. (C) 2009 Elsevier Ltd. All rights reserved,
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