5055-10-7Relevant articles and documents
Inter-and intramolecular annulation strategies to a cyclopentanone building block containing an all-carbon quaternary stereogenic center
Penrose, Stephen D.,Stott, Andrew J.,Breccia, Perla,Haughan, Alan F.,Bürli, Roland W.,Jarvis, Rebecca E.,Dominguez, Celia
supporting information, p. 1401 - 1404 (2015/03/30)
Synthesis of (S)-2-methyl-3-fluorophenyl cyclopentanone methyl ester (1S)-1 has been achieved by both inter-and intramolecular alkylation reactions on multigram scale, using chiral pool reagents. The intramolecular variant is a novel example of a chiral bis-electrophile reacting with a carbon nucleophile to form an enantiomerically pure all-carbon quaternary center.
HISTONE DEACETYLASE INHIBITORS AND COMPOSITIONS
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Paragraph 00143, (2014/10/15)
Provided are certain histone deacetylase (HDAC) inhibitors of Formula (I), compositions thereof, and methods of their use.
Synthesis of enantiopure 3-substituted pyrroline N-oxides by highly regioselective oxidation of the parent hydroxylamines: A mechanistic rationale
Goti, Andrea,Cicchi, Stefano,Fedi, Valentina,Nannelli, Luca,Brandi, Alberto
, p. 3119 - 3125 (2007/10/03)
The syntheses of four new, differently O-substituted 3-hydroxypyrroline N-oxides and the first 3-amino analogue have been performed by the use of a strategy involving double nucleophilic displacement of the corresponding dimesylates by hydroxylamine and oxidation of the resulting 1-hydroxypyrrolidines. The regioselectivity data of the oxidation reactions nicely confirm the mechanistic hypothesis, which explains the dependence on the electronic nature of the substituent. The trend of the regioselectivity ratio has useful predictive value. Practical complete regioselection has been obtained by substitution with a benzoyloxy functionality. The O-allyl-substituted nitrone is not stable in the reaction conditions, undergoing immediately an intramolecular cycloaddition reaction with complete stereocontrol and inversion of regio- and stereoselectivity with respect to the intermolecular case.