170969-90-1Relevant academic research and scientific papers
Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: Applications in the asymmetric synthesis of C(5)-substituted transpentacins
Davies, Stephen G.,Fletcher, Ai M.,Lee, James A.,Roberts, Paul M.,Souleymanou, Myriam Y.,Thomson, James E.,Zammit, Charlotte M.
, p. 2702 - 2728 (2014/05/06)
The diastereoselective Ireland-Claisen rearrangement of a range of substituted allyl β-amino esters gave the corresponding enantiopure α-substituted-β-amino esters with good diastereoselectivity. The application of this methodology in the asymmetric synthesis of a range of C(5)-substituted 1,2-anti-1,5-syn-transpentacins was demonstrated by the rearrangement of a range of β-amino esters derived from sorbic acid, followed by esterification, ring-closing metathesis, hydrogenolytic deprotection/reduction, and hydrolysis, which gave the C(5)-substituted transpentacins in only 9 steps from commercially available starting materials. This journal is the Partner Organisations 2014.
Double asymmetric induction as a mechanistic probe: The doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure α,β-unsaturated esters and enantiopure α,β-unsaturated hydroxamates
Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Thomson, James E.,Yin, Jingda
, p. 6382 - 6403 (2011/09/19)
The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to a range of enantiopure α,β-unsaturated esters [derived from Corey's 8-phenylmenthol chiral auxiliary] and enantiopure α,β-unsaturated hydroxamates [derived from our 'chiral Weinreb amide' auxiliary (S)-N-1-(1′-naphthyl)ethyl-O-tert- butylhydroxylamine] has been used as a mechanistic probe to determine the reactive conformations of these acceptors.
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.
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.
