82891-94-9Relevant articles and documents
Amidation of esters with amino alcohols using organobase catalysis
Caldwell, Nicola,Campbell, Peter S.,Jamieson, Craig,Potjewyd, Frances,Simpson, Iain,Watson, Allan J. B.
, p. 9347 - 9354 (2014)
A catalytic protocol for the base-mediated amidation of unactivated esters with amino alcohol derivatives is reported. Investigations into mechanistic aspects of the process indicate that the reaction involves an initial transesterification, followed by an intramolecular rearrangement. The reaction is highly general in nature and can be extended to include the synthesis of oxazolidinone systems through use of dimethyl carbonate.
Synthesis and anti-bacterial activity of a library of 1,2-benzisothiazol-3(2H)-one (BIT) derivatives amenable of crosslinking to polysaccharides
Viani, Fiorenza,Rossi, Bianca,Panzeri, Walter,Merlini, Luca,Martorana, Alessandra M.,Polissi, Alessandra,Galante, Yves M.
, p. 1745 - 1761 (2017/03/08)
1,2-Benzisothiazol-3(2H)-one (BIT) is one of the most common chemical biocides in industrial products, with a heterocyclic structure and a wide range of antimicrobial activity. A library of BIT derivatives was synthesized and characterized, from which 18 compounds were selected, tested for anti-bacterial activity relative to the parent molecule and amenable of coupling to plant polysaccharides in general and to galactomannans (GM) in particular, widely used as rheology modifiers, but with limited “biostability”. Four sites on the BIT core were targeted: the nitrogen and the oxygen atoms on the heterocyclic ring, the C5 and the C6 positions on the aromatic ring, where functional groups were introduced. The ultimate aim of this work is to establish whether by covalently linking a biocide to GM polymers, their “biostability” can be improved.
Palladium-catalyzed asymmetric alkylation in the synthesis of cyclopentanoid and cycloheptanoid core structures bearing all-carbon quaternary stereocenters
Hong, Allen Y.,Bennett, Nathan B.,Krout, Michael R.,Jensen, Thomas,Harned, Andrew M.,Stoltz, Brian M.
supporting information; experimental part, p. 10234 - 10248 (2012/01/03)
General catalytic asymmetric routes toward cyclopentanoid and cycloheptanoid core structures embedded in numerous natural products have been developed. The central stereoselective transformation in our divergent strategies is the enantioselective decarboxylative alkylation of seven-membered β-ketoesters to form α-quaternary vinylogous esters. Recognition of the unusual reactivity of β-hydroxyketones resulting from the addition of hydride or organometallic reagents enabled divergent access to γ-quaternary acylcyclopentenes through a ring contraction pathway or γ-quaternary cycloheptenones through a carbonyl transposition pathway. Synthetic applications of these compounds were explored through the preparation of mono-, bi-, and tricyclic derivatives that can serve as valuable intermediates for the total synthesis of complex natural products. This work complements our previous work with cyclohexanoid systems.
