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Synthesis and catalytic application of chiral 1,1'-Bi-2-naphthol- and biphenanthrol-based pincer complexes: selective allylation of sulfonimines with allyl stannane and allyl trifluoroborate.
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.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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2007 (English)In: Journal of Organic Chemistry, Vol. 72, no 13, 4689-4697 p.Article in journal (Refereed) Published
Abstract [en]

New easily accessible 1,1'-bi-2-naphthol- (BINOL-) and biphenanthrol-based chiral pincer complex catalysts were prepared for selective (up to 85% enantiomeric excess) allylation of sulfonimines. The chiral pincer complexes were prepared by a flexible modular approach allowing an efficient tuning of the selectivity of the catalysts. By employment of the different enantiomeric forms of the catalysts, both enantiomers of the homoallylic amines could be selectively obtained. Both allyl stannanes and allyl trifluoroborates can be employed as allyl sources in the reactions. The biphenanthrol-based complexes gave higher selectivity than the substituted BINOL-based analogues, probably because of the well-shaped chiral pocket generated by employment of the biphenanthrol complexes. The enantioselective allylation of sulfonimines presented in this study has important implications for the mechanism given for the pincer complex-catalyzed allylation reactions, confirming that this process takes place without involvement of palladium(0) species.

Place, publisher, year, edition, pages
2007. Vol. 72, no 13, 4689-4697 p.
Keyword [en]
chiral pincer complex assymetric allylation allylstannane allylborate boron
National Category
Other Basic Medicine
Identifiers
URN: urn:nbn:se:su:diva-22555DOI: doi:10.1021/jo070288b S0022-3263(07)00288-5OAI: oai:DiVA.org:su-22555DiVA: diva2:189082
Available from: 2008-01-04 Created: 2008-01-04 Last updated: 2011-01-11Bibliographically approved

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Publisher's full texthttp://pubs.acs.org/cgi-bin/abstract.cgi/joceah/2007/72/i13/abs/jo070288b.html

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