156406-13-2Relevant articles and documents
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.
Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate for the asymmetric synthesis of (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin
Abraham, Elin,Davies, Stephen G.,Docherty, Alexander J.,Ling, Kenneth B.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.,Toms, Steven M.
, p. 1356 - 1362 (2008/12/20)
Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate with a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide and lithium (R)-N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)amide provides an efficient entry to the corresponding homochiral methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tris(phenylthio)methyl-cyclopentane-carboxylate derivatives in >98% de, with subsequent, sequential desulfurisation with Raney Nickel, N-debenzylation and ester hydrolysis furnishing (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin in high yield, >98% de and >98% ee.
