717137-46-7Relevant academic research and scientific papers
Doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure N-enoyl oxazolidin-2-ones: A mechanistic probe
Davies, Stephen G.,Fletcher, Ai M.,Hermann, Gesine J.,Poce, Giovanna,Roberts, Paul M.,Smith, Andrew D.,Sweet, Miles J.,Thomson, James E.
experimental part, p. 1635 - 1648 (2010/10/18)
The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to a range of enantiopure N-enoyl oxazolidin-2-ones has been used as a mechanistic probe to determine that the reactive conformation is the anti-s-cis form. The β-amino carbonyl products resulting from these conjugate addition reactions are useful templates for further elaboration into an α,β,α-pseudotripeptide.
Asymmetric three- and [2 + 1]-component conjugate addition reactions for the stereoselective synthesis of polysubstituted piperidinones
Davies, Stephen G.,Roberts, Paul M.,Smith, Andrew D.
, p. 1405 - 1415 (2008/02/10)
The efficiency and stereoselectivity of the conjugate addition of lithium (Z)- or (E)-β-amino ester enolates, generated by lithium amide conjugate addition to an α,β-unsaturated ester or deprotonation of a β-amino ester, respectively, to a range of α,β-unsaturated acceptors has been investigated. Deprotonation of a β-amino ester with LDA, followed by conjugate addition to a chiral α,β-unsaturated oxazolidinone gives high 2,3-anti selectivity (～90% d.e.), with hydrogenolysis and purification to homogeneity generating stereodefined trisubstituted piperidinones as single stereoisomers. Asymmetric three-component couplings of α,β-unsaturated esters and alkylidene malonates initiated by lithium amide conjugate addition proceeds with high levels of 2,3-anti stereoselectivity, with hydrogenolysis giving tetrasubstituted piperidinones. This journal is The Royal Society of Chemistry.
Double asymmetric induction as a mechanistic probe: Conjugate addition for the asymmetric synthesis of a pseudotripeptide
Davies, Stephen G.,Hermann, Gesine J.,Sweet, Miles J.,Smith, Andrew D.
, p. 1128 - 1129 (2007/10/03)
Double asymmetric induction as a mechanistic probe indicates that, for the conjugate addition of (R)- and (S)-lithium N-benzyl-N-α-methylbenzylamide to (S)-3′-phenylprop-2′-enoyl-4-benzyloxazolidinone, the reactive conformation of the N-acyl oxazolidinone is the anti-s-cis form, facilitating the asymmetric synthesis of a pseudotripeptide.
