Probing the effect of allylic substitution on cyclic ammonium ylid rearrangementsSançon, J. and Sweeney, J. B. (2010) Probing the effect of allylic substitution on cyclic ammonium ylid rearrangements. Synlett, 2010 (4). pp. 664-666. ISSN 1437-2096 Full text not archived in this repository. It is advisable to refer to the publisher's version if you intend to cite from this work. See Guidance on citing. To link to this item DOI: 10.1055/s-0029-1219348 Abstract/SummaryThe [2,3]-sigmatropic rearrangement of tetrahydropyridine-derived ammonium ylids is a valuable method for the preparation of substituted pyrrolidine carboxylates. The presence of an allylic substituent does not intrinsically reduce the yield of rearrangements, and the diastereoselectivity of rearrangement is related to the structure of the diazo reactant. The method represents a very rapid means of accessing complex pyrrolidines, as shown by preparation of a precursor to the core of lactacystin.
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