831-69-6Relevant articles and documents
Regio- and Stereoselective Chan-Lam-Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines
Steemers, Luuk,Wijsman, Linda,van Maarseveen, Jan H.
supporting information, p. 4241 - 4245 (2018/10/02)
Efficient and scalable Cu(II)-mediated enol esterification methodology of carboxylic acids from alkenyl boroxines and boronic acids is presented. The reaction shows a wide scope in aliphatic and aromatic carboxylic acids in combination with several alkenyl boroxines. In the case of 2-substituted alkenyl boroxines the double bond configuration was fully retained in the enol ester product. Also N-hydroxyimides and imides could be transformed in the respective amidooxy vinyl enol ethers and vinyl enamides. Finally, with the exception of methionine, all other 19 canonical amino acids showed their compatibility to give the enol esters in a stereoselective fashion. (Figure presented.).
Ethenolate transfer reactions: A facile synthesis of vinyl esters
Appaye, Srinivasan Kaliyaperumal,Nikumbh, Satish Pandurang,Govindapur, Rajeshwar Reddy,Banerjee, Shyamapada,Bhalerao, Dinesh S.,Kumar, Unniaran K. Syam
, p. 1115 - 1122 (2014/09/17)
A simple and efficient metal-free ethenolate transfer reaction has been elaborated in moderate-to-high yields from vinyl acetate. This reaction was accomplished by generation of potassium ethenolate, which was then reacted with homo and mixed anhydrides of aliphatic, aryl and heteroaryl acids, to yield the corresponding vinyl esters. The utility of thus generated vinyl esters was then probed by carrying out intramolecular Heck reactions to give isobenzofuran-1(3H)-one derivatives in excellent yields. Copyright
Dinuclear zinc-catalyzed asymmetric desymmetrization of acyclic 2-substituted-1,3-propanediols: A powerful entry into chiral building blocks
Trost, Barry M.,Malhotra, Sushant,Mino, Takashi,Rajapaksa, Naomi S.
supporting information; experimental part, p. 7648 - 7657 (2009/08/19)
The asymmetric acylation of meso-2-substituted-1,3-propanediols by using an amphoteric chiral dinuclear zinc catalyst is described. It is has been demonstrated that both 2-alkyl- and 2-aryl-1,3-propanediols can be desymmetrized in high yields and enantioselectivities by using the same family of ligands. Given that both antipodes of the chiral catalyst are available, both enantiomers of the desymmetrized product can be obtained from the same starting material. The synthetic utility of the desymmetrized products has been demonstrated by the synthesis of several chiral building blocks with high enantiomeric purities.
