103660-95-3Relevant academic research and scientific papers
Stereocontrolled Thio-Claisen rearrangement of S-allylic ketene aminothioacetals by an hydroxysubstituted adjacent stereogenic centre
Beslin, Pierre,Lelong, Bruno
, p. 17253 - 17264 (2007/10/03)
(Z)-S-alkylic ketene aminothioacetals were prepared from N,N-Dimethyl β-hydroxythioamides 2-8 by deprotonation with LDA (2 eq.) at -78°C followed by S-alkylation with allylic bromide. Rearrangement of these compounds occured easily at room temperature affording major syn N,N-dimethyl β-hydroxy α-allylic thioamides 9-21 with a syn/anti ratio of 80/20 to 98/2. The syn configuration of the major diastereoisomer was confirmed by an univocal synthesis of syn thioamides 9 and 11. The structure assignments were confirmed by empirical 13C NMR rules. The observed induction is well suppported by a proposed transition state model.
ASYMMETRIC SYNTHESIS OF β-HYDROXYTHIOACETAMIDES MEDIATED BY ENANTIOMERICALLY PURE SULPHINYL DERIVATIVES.
Cinquini, Mauro,Manfredi, Amedea,Molinari, Henriette,Restelli, Angelo
, p. 4929 - 4936 (2007/10/02)
Enantiomerically pure p-tolyl sulphinyl-N,N-dimethylthioacetamide (1) was prepared starting from (-)-(S)-menthyl toluene-p-sulphinate.Aldol-type condensation of (1) and subsequent removal of the sulphinyl group open an entry to optically active β-hydroxy thioacetamides in 40-90percent e.e.
C-C ASYMMETRIC BOND FORMATION MEDIATED BY OPTICALLY ACTIVE SULFOXIDES
Cinquini, Mauro
, p. 39 - 72 (2007/10/02)
Highly stereoselective C-C bond forming reactions can be performed with a variety of optically active sulfinyl derivatives to afford, after desulfurization, optically active sulfur-free products.
