159573-36-1Relevant articles and documents
Preparation of both enantiomers of 2-methyl-3-hydroxythioesters based on chiral Lewis acid-controlled synthesis
Kobayashi, Shu,Horibe, Mineko
, p. 7277 - 7286 (1996)
Both enantiomers of 2-methyl-3-hydroxythioesters have been synthesized by using chiral tin(II) Lewis acid-mediated aldol reactions of (Z)-1-ethylthio-1-trimethylsiloxypropene (4) with aldehydes, based on chiral Lewis acid-controlled synthesis. The key to
Molecular recognition by artificial chiral catalysts utilizing a metal chelate. A remarkable difference in reactivity between geometrical isomers of silyl enolates in asymmetric aldol reactions using chiral Tin(II) catalysts
Kobayashi,Horibe,Hachiya
, p. 3173 - 3176 (2007/10/02)
A remarkable difference in reactivity between (E)- and (Z)-enolates in the asymmetric aldol reactions of silyl enolates with adehydes using chiral tin(II) Lewis acids was found. This difference can be interpreted to mean that the chiral catalyst coordinat
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.