1448055-26-2Relevant articles and documents
The asymmetric synthesis of enantiopure C(5)-substituted transpentacins via diastereoselective conjugate additions to a β′-amino-α,β-unsaturated ester
Davies, Stephen G.,Fletcher, Ai M.,Roberts, Paul M.,Thomson, James E.,Zammit, Charlotte M.
, p. 208 - 221 (2020/01/31)
The asymmetric synthesis of a range of 1,2-anti-1,5-syn-transpentacins, bearing either alkyl, phenyl or hydroxymethyl substituents at the C(5)-position, has been achieved using the diastereoselective conjugate additions of Grignard reagents to an enantiopure β′-amino-α,β-unsaturated ester as the key step. In addition, the doubly diastereoselective conjugate addition of an enantiopure lithium amide reagent to the β′-amino-α,β-unsaturated ester provided access to the corresponding β,β′-diamino ester, which was subsequently converted to both (S,S)-(2,5-diaminocyclopent-1-yl)methanol and (S,S)-2,5-diaminocyclopentane-1-carboxylic acid. In each case, the final enantiopure products were obtained as single diastereoisomers (>99:1 dr) in good yields over five steps or fewer from commercially available starting materials.
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.
Asymmetric syntheses of enantiopure C(5)-substituted transpentacins via diastereoselective Ireland-Claisen rearrangements
Davies, Stephen G.,Fletcher, Ai M.,Roberts, Paul M.,Thomson, James E.,Zammit, Charlotte M.
, p. 7037 - 7039 (2013/09/02)
Asymmetric syntheses of (S,S,S)-2-amino-5-methylcyclopentanecarboxylic acid and (S,S,S)-2-amino-5-phenylcyclopentanecarboxylic acid were achieved in 9 steps from commercially available starting materials via the Ireland-Claisen rearrangement of two enanti
