Asymmetric synthesis of β-amino-γ-substituted-γ-butyrolactones: Double diastereoselective conjugate addition of homochiral lithium amides to homochiral α,β-unsaturated esters was written by 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.. And the article was included in Organic & Biomolecular Chemistry in 2007.Quality Control of 5,5-Dimethyloxazolidin-2-one This article mentions the following:
Nonracemic α,β-unsaturated esters such as I (R = Me, Ph; TBS = tert-butyldimethylsilyl) containing a single, γ-stereogenic center undergo stereoselective addition of lithium amides derived from nonracemic benzylamines (with or without concomitant alkylation reactions) to give β-amino esters such as (benzylamino)pentanoates II (R = Me, Ph; R1 = H, Me). The stereoisomers produced by the additions of lithium N-(α-methylbenzyl)-N-benzylamides to nonracemic γ-substituted-α,β-unsaturated esters such as I are determined by the configurations of the amides, while the relative stereochem. of the ester and the amide determines the level of stereoselectivity observed The stereoselectivities of the additions of lithium N-(α-methylbenzyl)-N-benzylamides to a nonracemic γ-substituted-α,β-unsaturated enoyl oxazolidinone is opposite to those observed in the additions of lithium N-(α-methylbenzyl)-N-benzylamides to nonracemic γ-substituted-α,β-unsaturated esters with the same configurations at the γ stereocenter. Desilylation and cyclization (with or without epimerization) of the resultant β-amino carbonyl compounds provides nonracemic β-amino-γ-lactones such as III (R = Me, Ph; R1 = H, Me) with good yields and high diastereoselectivities. In the experiment, the researchers used many compounds, for example, 5,5-Dimethyloxazolidin-2-one (cas: 1121-83-1Quality Control of 5,5-Dimethyloxazolidin-2-one).
5,5-Dimethyloxazolidin-2-one (cas: 1121-83-1) belongs to oxazolidine derivatives. A common way to produce multisubstituted oxazolidines is by means of cycloaddition reactions. As well as other multifunctional heterocyclic compounds, oxazolidine rings play an essential role in organic and medicinal chemistry, behaving, in some cases as powerful antitumor agents.Quality Control of 5,5-Dimethyloxazolidin-2-one
Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem