151764-53-3Relevant articles and documents
4-Isopropyl-2-oxazolin-5-one anion as masked umpoled synthon for both formyl and hydroxycarbonyl anions: Generation, reactivity and synthetic applications
Barco, Achille,Benetti, Simonetta,De Risi, Carmela,Pollini, Gian P.,Spalluto, Giampiero,Zanirato, Vinicio
, p. 4719 - 4734 (2007/10/03)
The anion of the title compound, simply generated in the presence of catalytic amount of triethylamine, reacts with both common electrophilic olefins and aldehydes to give moderate to good yield of Michael or aldol adducts respectively. Mild acid treatment of these adducts at ambient temperature serves to demask the aldehyde function, allowing one to consider the anion of 1 as a nucleophilic acylating equivalent of formaldehyde. On the other hand, the same anion of 1 may act as a masked umpoled synthon for a hydroxycarbonyl anion since its aldol adducts with aldehydes undersent concomitant isomerization and ring cleavage under mild basic conditions producing dipeptides which could be hydrolyzed to give the corresponding carboxylic acids. Synthetic applications of this chemistry in the area of sugar, aminosugar and non-proteinogenic aminoacid derivatives are discussed.
Enantioselective synthesis of the taxol and taxotere side chains
Koskinen,Karvinen,Siirila
, p. 21 - 22 (2007/10/02)
A new route to Taxol and Taxotere side chains via asymmetric dihydroxylation of both cis and transmethyl cinnamates is described.
Asymmetric Synthesis of Homochiral syn- and anti-3-Phenylisoserine Derivatives: A Practical Strategy for the Synthesis of the Taxol C-13 Side Chain
Bunnage, Mark E.,Davies, Stephen G.,Goodwin, Christopher J.
, p. 1375 - 1376 (2007/10/02)
A tandem lithium amide conjugate addition-electrophilic hydroxylation approach to the synthesis of N-benzoyl-3-phenylisoserine methyl esters affords a strategy for the practical synthesis of the taxol side chain.