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Lewis acid mediated...
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Blid, JanKTH,Organisk kemi
(author)
Lewis acid mediated asymmetric 2,3 -sigmatropic rearrangement of allylic amines. Scope and mechanistic investigation
- Article/chapterEnglish2007
Publisher, publication year, extent ...
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2007-01-17
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American Chemical Society (ACS),2007
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printrdacarrier
Numbers
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LIBRIS-ID:oai:DiVA.org:kth-16374
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https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-16374URI
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https://doi.org/10.1021/jo062178vDOI
Supplementary language notes
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Language:English
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Summary in:English
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Classification
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Subject category:ref swepub-contenttype
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Subject category:art swepub-publicationtype
Notes
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QC 20100525
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[GRAPHIC] The first asymmetric [2,3]-sigmatropic rearrangement of achiral allylic amines has been realized by quaternization of the amines with an enantiomerically pure diazaborolidine and subsequent treatment with Et3N. The resultant homoallylic amines were obtained in good yields and excellent ee's. The observed diastereo- and enantioselectivities were rationalized by invoking a kinetically controlled process, and support for this model was obtained from an NMR spectroscopic investigation of the chiral Lewis acid-substrate complex. The structure of the Lewis acid-product complex was established by X-ray crystallographic analysis and supported the proposed mechanism.
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Added entries (persons, corporate bodies, meetings, titles ...)
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Panknin, OlafKTH,Organisk kemi(Swepub:kth)u1qdmpib
(author)
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Tuzina, PavelKTH,Organisk kemi(Swepub:kth)u1pekxkz
(author)
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Somfai, PeterKTH,Organisk kemi(Swepub:kth)u1ddelvn
(author)
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KTHOrganisk kemi
(creator_code:org_t)
Related titles
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In:Journal of Organic Chemistry: American Chemical Society (ACS)72:4, s. 1294-13000022-32631520-6904
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