Regio- and stereoselective synthesis of 1,3-aminoalcohol derivatives from allylamine derivatives via internal sulfinyl group participation

Synthesis of a novel series of 2,3,4-trisubstituted oxazolidines designed by isosteric replacement or rigidification of the structure and cytotoxic evaluation

“…Pellicciari's group reported that J CH]CH was 15.8 Hz for this compound while Raghavan's group found 12.2 Hz. 27,28 In our case, J CH]CH values for E-and Z-olen (4 and 3, X ¼ NO 2 , S isomer) were 16.0 and 11.6 Hz, respectively (Fig. 6).…”

“…Treatment of phosphonium salt 11 with BuLi followed by addition of Garner's aldehyde 10 gave olens 3 and 4 in 70% yield as an isomer mixture which were separated by preparative TLC (Z/E 6 : 4). 27 Some controversy about the coupling constants (J) in 1 H NMR This journal is © The Royal Society of Chemistry 2014 spectra was found in previously published studies. Unsubstituted E-olens (X ¼ H) with the R conguration was previously reported in the literature.…”

Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors

“…Concomitant cleavage of the N ‐tosyl and acetate group of 22 delivered the claimed (1 R ,3 R )‐HPA‐12. It is noteworthy that even if the stereochemical assignment of bromo‐alcohol 17 appears to be firmly argued, the characterization of the final HPA‐12, in particular regarding its optical rotation, seems to advocate for a 1 R ,3 S absolute configuration.…”

New 1,3-amino alcohols derived from enantiopure bridgehead β-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acids

“…They constitute convenient starting materials for the synthesis of various 1,3-heterocycles for example (Ager et al 1996;Fülöp et al 1997;Gyonfalvi et al 2003;Kivelä et al 2003Kivelä et al , 2005. Although 1,2-amino alcohols have received much attention because they are generally readily accessible in enantiomerically pure form from natural precursors (Gyonfalvi et al 2003;Reetz et al 1987;Delair et al 1994;Masui and Shiori 1998;Laczkowski et al 2009;, the synthesis and the use of chiral 1,3-amino alcohols are still undergoing development and remain a challenge (Lait et al 2007;Didier et al 1991; Barluenga et al 1993; Bartoli et al 1994;Kossenjans and Martens 1999;Kochi et al 2003;Raghavan et al 2004;Murai et al 2005;Balazs et al 2007). …”