138175-92-5Relevant academic research and scientific papers
Performance of SCS palladium pincer complexes in borylation of allylic alcohols. Control of the regioselectivity in the one-pot borylation-allylation process
Selander, Nicklas,Szabo, Kalman J.
, p. 5695 - 5698 (2009)
(Chemical Equation Presented) One-pot borylation-allylation reactions of aldehydes and allylic alcohols were performed under various reaction conditions. The borylation of allylic alcohols was performed using a very efficient SCS palladium pincer-complex catalyst. The regioselectivity of the allylation depends on the applied solvent. The reaction in CHCl3 gave the linear allylic product; however, when MeOH was added to the reaction mixture, the branched allylic product was formed.
Development of a highly α-regioselective metal-mediated allylation reaction in aqueous media: New mechanistic proposal for the origin of α-homoallylic alcohols
Tan, Kui-Thong,Chng, Shu-Sin,Cheng, Hin-Soon,Loh, Teck-Peng
, p. 2958 - 2963 (2007/10/03)
This paper described a general method to obtain α-adduct homoallylic alcohols using indium, zinc, and tin in water. A new mechanism was proposed to account for the formation of these synthetically difficult-to-obtain molecules. Generally, this method can
Development of a highly α-regioselective indium-mediated allylation reaction in water
Loh, Teck-Peng,Tan, Kui-Thong,Yang, Jian-Ying,Xiang, Chao-Li
, p. 8701 - 8703 (2007/10/03)
Linear α homoallylic alcohol adducts were obtained with high regioselectivities in moderate to good yields using allylic indium reagents in the presence of 10 M water. The exceptionally high regioselectivities observed were neither steric nor electronic i
The first In(OTf)3-catalyzed conversion of kinetically formed homoallylic alcohols into the thermodynamically preferred regioisomers: Application to the synthesis of 22α-sterols
Loh, Teck-Peng,Tan, Kui-Thong,Hu, Qi-Ying
, p. 2921 - 2922 (2007/10/03)
A retro-ene reaction that generates the parent aldehyde and a sigmatropic rearrangement are involved in the In(OTf)3-catalyzed conversion of homoallylic alcohols 1 into the thermodynamically favored regioisomers 2. This method can be used for the stereocontrolled synthesis of linear homoallylic 22α-sterols from their readily accessible branched 22β isomers.
HYDROZIRCONATION / TRANSMETALATION / ALKYLATION: DIRECT ONE-POT CONVERSION OF 1-ALKYNES TO E-1,2-DISUBSTITUTED ALKENES
Lipshutz, Bruce H.,Kato, Kaneyoshi
, p. 5647 - 5650 (2007/10/02)
Hydrozirconation of terminal acetylenes followed by transmetalation of the intermediate vinyl zirconate with a higher order cyanocuprate affords mixed vinylic cuprates which undergo alkylations with a variety of electrophiles.
