1003280-22-5Relevant academic research and scientific papers
Asymmetric synthesis of β-amino-γ-substituted-γ- butyrolactones: Double diastereoselective conjugate addition of homochiral lithium amides to homochiral α,β-unsaturated esters
Cailleau, Thais,Cooke, Jason W. B.,Davies, Stephen G.,Ling, Kenneth B.,Naylor, Alan,Nicholson, Rebecca L.,Price, Paul D.,Roberts, Paul M.,Russell, Angela J.,Smith, Andrew D.,Thomson, James E.
, p. 3922 - 3931 (2008/09/21)
Chiral α,β-unsaturated esters, containing a single, γ-stereogenic centre, show modest levels of substrate control upon conjugate addition of lithium dibenzylamide. Double diastereoselective conjugate additions of homochiral lithium N-benzyl-N-(α-methylbenzyl)amide to the homochiral α,β-unsaturated esters display matching and mismatching effects. In each case, however, these additions proceed under the dominant stereocontrol of the lithium amide to give the corresponding β-amino esters in high de. A remarkable reversal in stereoselectivity is noted by changing the ester functionality to an oxazolidinone. Subsequent O-deprotection and cyclisation of the resultant β-amino adducts gives access to the corresponding β-amino-γ-substituted-γ- butyrolactones in good yield and high de. This journal is The Royal Society of Chemistry.
