Alfie, Rachel J. published the artcileA kinetically controlled direct aldol addition of ¦Á-chloro thioesters via soft enolization, Category: catalysis-chemistry, the publication is Tetrahedron Letters (2017), 58(3), 185-189, database is CAplus.
¦Á-Chloro thioesters such as ClCH2COSR (R = 2,4,6-i-Pr3C6H2)(I) underwent diastereoselective aldol additions to aldehydes R1CHO [R1 = 2-naphthyl, Ph, t-Bu, cyclohexyl, i-Pr, PhCH2CH2, Me(CH2)6] in the presence of MgBr2¡¤OEt2 and i-Pr2NEt in CH2Cl2 at -78¡ã to give the syn-aldol adducts II [R1 = 2-naphthyl, Ph, t-Bu, cyclohexyl, i-Pr, PhCH2CH2, Me(CH2)6] as the major products in 40-80% yields and in 2:1-11:1 dr. Both enolizable and nonenolizable aldehydes underwent chemo- and stereoselective aldol addition under these conditions. At -78¡ã, the reactions are kinetically controlled, as shown by the lack of aldehyde exchange when p-tolualdehyde and an aldol adduct were submitted to the reaction conditions at -78¡ã. Aldol addition of I to (S)-i-PrCH(OTBDMS)CHO (TBDMS = tert-butyldimethylsilyl) at either -78¡ã or 24¡ã yielded III (R2 = COSR) as a single diastereomer. The structure of III (R2 = HOCH2) was determined by X-ray crystallog.
Tetrahedron Letters published new progress about 22693-41-0. 22693-41-0 belongs to catalysis-chemistry, auxiliary class Other Functionalization Reagent, name is 2,4,6-Triisopropylbenzenethiol, and the molecular formula is C15H24S, Category: catalysis-chemistry.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia