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Shyam, Pranab K.,Jang, Hye‐,Young WILEY‐VCH Verlag 2014 European Journal of Organic Chemistry Vol.2014 No.9
<P><B>The cover picture shows </B>an easy and efficient transformation of cinnamaldehyde and its derivatives to optically active β‐azido α‐oxyaminated aldehydes by the cooperation of an organocatalyst (chiral sec‐amine) and an iron catalyst. Furthermore, synthesized β‐azido α‐oxyaminated aldehydes were easily modified to afford pharmaceutically valuable β‐amino α‐hydroxy esters in three steps without loss of enantio‐ and diastereoselectivity. Details are discussed in the Short Communication by P. K. Shyam and H.‐Y. Jang on p. 1817 ff. </P>
Shyam, Pranab K.,Jang, Hye‐,Young WILEY‐VCH Verlag 2014 EUROPEAN JOURNAL OF ORGANIC CHEMISTRY Vol.2014 No.9
<P>The tandem reaction of ,-unsaturated aldehydes with trimethylsilyl azide and 2,2,6,6-tetramethylpiperidin-1-yloxy in the presence of chiral amines and iron complexes as the catalysts in a one-pot reaction enantioselectively afforded -azido -oxyaminated aldehydes. Further synthetic modification of the product afforded -amino -hydroxy esters in good yields with good diastereo- and enantioselectivities.</P>
Copper-catalyzed Oxidative Olefination of Thiols Using Sulfones and Phosphorous Ylides
Pranab K.Shyam,이찬,장혜영 대한화학회 2015 Bulletin of the Korean Chemical Society Vol.36 No.7
Copper-catalyzed one-pot conversion of thiols to olefins was conducted under aerobic conditions. Thiols were oxidized to generate thioaldehydes, which reacted with sulfones or phosphorous ylides to form the corresponding olefins. The formation of thiosulfonates and phosphorous sulfides confirms that these olefination protocols proceed via thioaldehyde-sulfone and thioaldehyde-ylide adducts.
Shyam, Pranab K.,Jang, Hye-Young American Chemical Society etc. 2017 Journal of organic chemistry Vol.82 No.3
<P>Simple and high-yielding strategies for the production of a variety of sulfones and sulfonamides, using thiosulfonates synthesized by copper-catalyzed aerobic dimerization, are reported. Although thiosulfonates are an old class of compound, practical methods for their synthesis and utilization have not been rigorously developed. In this study, we revisit the reactions of easily accessible thiosulfonates to form sulfinate anions. Because of the similar reactivity of thiosulfonates and metal sulfinates derived from toxic SOD thiosulfinates are proposed to be stable, nontoxic alternatives to metal sulfinate salts.</P>
Shyam, Pranab K.,Kim, Yu Kwon,Lee, Chan,Jang, Hye‐,Young WILEY-VCH 2016 Advanced Synthesis & Catalysis Vol.358 No.1
<P><B>Abstract</B></P><P>Copper‐catalyzed aerobic coupling of thiols and alcohols affords sulfinates and thiosulfonates. These products are assumed to form <I>via</I> sulfinyl radicals which are not commonly found in oxidative coupling reactions of thiols. A reaction mechanism involving sulfinyl radicals is proposed, and mass and electron paramagnetic resonance (EPR) experimental results are provided.</P>
Synthesis of Vinyl Sulfones via I2‐mediated Alkene Sulfonylations with Thiosulfonates
황상준,Pranab K.Shyam,장혜영 대한화학회 2018 Bulletin of the Korean Chemical Society Vol.39 No.4
A simple sulfonylation strategy involving I2 and thiosulfonates, as sulfonyl‐group precursors, is reported for the synthesis of vinyl sulfones. Sulfonyl radicals are presumed to be generated from thiosulfonates, which subsequently react with styrene or cinnamic acid derivatives to afford a variety of vinyl sulfones under the described reaction conditions. Detailed conditions, the substrate scope, and mechanistic studies are discussed.