40076-53-7Relevant articles and documents
Stereospecific Asymmetric Synthesis of Tertiary Allylic Alcohol Derivatives by Catalytic [2,3]-Meisenheimer Rearrangements
Yu, Xin,Wannenmacher, Nick,Peters, René
supporting information, p. 10944 - 10948 (2020/05/04)
Chiral acyclic tertiary allylic alcohols are very important synthetic building blocks, but their enantioselective synthesis is often challenging. A major limitation in catalytic asymmetric 1,2-addition approaches to ketones is the enantioface differentiation by steric distinction of both ketone residues. Herein we report the development of a catalytic asymmetric Meisenheimer rearrangement to overcome this problem, as it proceeds in a stereospecific manner. This allows for high enantioselectivity also for the formation of products in which the residues at the generated tetrasubstituted stereocenter display a similar steric demand. Low catalyst loadings were found to be sufficient and the reaction conditions were mild enough to tolerate even highly reactive functional groups, such as an enolizable aldehyde, a primary tosylate, or an epoxide. Our investigations suggest an intramolecular rearrangement pathway.
An efficient DABCO-catalyzed Ireland-Claisen rearrangement of allylic acrylates
Li, Yunxia,Wang, Quanrui,Goeke, Andreas,Fráter, Georg
, p. 288 - 292 (2007/10/03)
A novel DABCO-catalyzed Ireland-Claisen [3,3]-rearrangement of allylic acrylates to give α-methylene-γ,δ-unsaturated carboxylic acids in the presence of an excess of TMSCl and DBU in refluxing acetonitrile was developed. The protocol provides an easy entry to α-methylene-γ, δ-unsaturated carboxylic acids from allylic alcohols in good yields. Georg Thieme Verlag Stuttgart.
Catalytic hydromagnesation of di- and polymethyl-substituted 1,3-butadienes
Viktorov,Zubritskii
, p. 1755 - 1765 (2007/10/03)
Hydromagnesation of di- and polymethyl-substituted 1,3-butadienes with alkylmagnesium halides in the presence of Ni(PPh3)2Cl2 and NiPy4Cl2 was studied.