104-30-3Relevant articles and documents
Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio-and Stereoselective Acylation of Alcohols
Koszelewski, Dominik,Brodzka, Anna,Madej, Arleta,Trzepizur, Damian,Ostaszewski, Ryszard
, p. 6331 - 6342 (2021/05/06)
Geminal diacetates have been used as sustainable acyl donors for enzymatic acylation of chiral and nonchiral alcohols. Especially, it was revealed that geminal diacetates showed higher reactivity than vinyl acetate for hydrolases that are sensitive to acetaldehyde. Under optimized conditions for enzymatic acylation, several synthetically relevant saturated and unsaturated acetates of various primary alcohols were obtained in very high yields up to 98% without E/Z isomerization of the double bond. Subsequently, the acyl donor was recreated from the resulting aldehyde and reused constantly in acylation. Therefore, the developed process is characterized by high atomic efficiency. Moreover, it was shown that acylation using geminal diacetates resulted in remarkable regioselectivity by discriminating among the primary and secondary hydroxyl groups in 1-phenyl-1,3-propanediol providing exclusively 3-acetoxy-1-phenyl-propan-1-ol in good yield. Further, enzymatic kinetic resolution (EKR) and chemoenzymatic dynamic kinetic resolution (DKR) protocols were developed using geminal diacetate as an acylating agent, resulting in chiral acetates in high yields up to 94% with enantiomeric excesses exceeding 99%.
An efficient one-pot synthesis of unsymmetrical ethers: A directly reductive deoxygenation of esters using an InBr3/Et3SiH catalytic system
Sakai, Norio,Moriya, Toshimitsu,Konakahara, Takeo
, p. 5920 - 5922 (2008/02/09)
(Chemical Equation Presented) This study describes a novel one-pot procedure for a directly reductive conversion of the carbonyl function of esters to the corresponding ethers by Et3SiH in the presence of a catalytic amount of InBr3.
Scandium(III) trifluoromethanesulfonate catalyzed aromatic nitration with inorganic nitrates and acetic anhydride
Kawada, Atsushi,Takeda, Shigemitsu,Yamashita, Kazumi,Abe, Hitoshi,Harayama, Takashi
, p. 1060 - 1065 (2007/10/03)
The rare earth metal(III) trifluoromethanesulfonate (rare earth metal(III) triflate, RE(OTf)3) was found to be an efficient catalyst for aromatic nitration with carboxylic anhydride-inorganic nitrate as the nitrating agent. In the presence of a catalytic amount of RE(OTf)3, the nitration of substituted benzenes proceeded to afford the corresponding nitrobenzenes. Especially, scandium(III) trifluoromethanesulfonate (scandium(III) triflate, Sc(OTf)3) is the most active catalyst among our tested Lewis acids. It was also found that acetic anhydride-Al(NO 3) · 9H2O is the most active nitrating agent in this system.