132333-71-2Relevant academic research and scientific papers
Diastereo- and Enantioselective Synthesis of syn- and anti-1,2-Diol Units by Asymmetric Aldol Reactions
Mukaiyama, Teruaki,Shiina, Isamu,Uchiro, Hiromi,Kobayashi, Shu
, p. 1708 - 1716 (2007/10/02)
syn- and anti-1,2-Diol units were prepared by using asymmetric aldol reactions of the silyl enol ethers derived from α-alkoxythioacetic S-esters with aldehydes.In the presence of tin(II) triflate, a chiral diamine, and dibutyltin diacetate, (Z)-2-benzyloxy-1-ethylthino-1-(trimethylsiloxy)ethene reacted with aldehydes to afford the corresponding anti-aldol adducts in high yields with excellent diastereo- and enantioselectivities, while syn-adducts were obtained from (Z)-2-(t-butyldimethylsiloxy)-1-ethylthio-1-(trimethylsiloxy)ethene and aldehydes under the same reaction conditions.Thus, both diastereomers can be synthesized in excellent enantiomeric excesses by simply choosing the protective groups of the alkoxyl parts of the silyl enol ethers.
A Conversion and Versatile Route for the Stereoselective Synthesis of Monosaccharides via Key Chiral Synthons Prepared from Achiral Sources
Mukaiyama, Teruaki,Shiina, Isamu,Kobayashi, Shu
, p. 2201 - 2204 (2007/10/02)
Three types of sugars, 6-deoxy-L-tallose, 4-C-methyl-D-ribose, and D-ribose were synthesized from both achiral starting materials, α,β-unsaturated aldehydes and silyl enol ethers of α-benzyloxy thioesters, by successive asymmetric aldol and vicinal dihydr
