63220-36-0Relevant articles and documents
On the structure of palau'amine: Evidence for the revised relative configuration from chemical synthesis
Lanman, Brian A.,Overman, Larry E.,Paulini, Ralph,White, Nicole S.
, p. 12896 - 12900 (2007)
Hexacyclic congeners 3 and 4 of palau'amine, which incorporate both guanidine functional groups and have the cis configuration of the azabicyclo[3.3.0]octane core, are prepared in 14 steps from cycloadduct 6. Synthetic access to these analogues allows the
UREA AND GUANIDINIUM DERIVATIVES OF IMINOSUGARS
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Paragraph 78, (2014/02/16)
The invention relates to novel urea and guanidinium derivatives of deoxynojirimycin and related iminosugars, wherein the ring nitrogen in the iminosugars is derivatised, methods for the preparation urea and guanidinium derivatives of deoxynojirimycin, (pr
Transition-state charge stabilization through multiple non-covalent interactions in the guanidinium-catalyzed enantioselective claisen rearrangement
Uyeda, Christopher,Jacobsen, Eric N.
supporting information; experimental part, p. 5062 - 5075 (2011/06/23)
The mechanism by which chiral arylpyrrole-substituted guanidinium ions promote the Claisen rearrangement of O-allyl α-ketoesters and induce enantioselectivity was investigated by experimental and computational methods. In addition to stabilization of the developing negative charge on the oxallyl fragment of the rearrangement transition state by hydrogen-bond donation, evidence was obtained for a secondary attractive interaction between the π-system of a catalyst aromatic substituent and the cationic allyl fragment. Across a series of substituted arylpyrrole derivatives, enantioselectivity was observed to vary predictably according to this proposal. This mechanistic analysis led to the development of a new p-dimethylaminophenyl-substituted catalyst, which afforded improvements in enantioselectivity relative to the parent phenyl catalyst for a representative set of substrates.
