6934-77-6Relevant academic research and scientific papers
Photoorganocatalytic synthesis of lactones: Via a selective C-H activation-alkylation of alcohols
Kaplaneris, Nikolaos,Bisticha, Aikaterini,Papadopoulos, Giorgos N.,Limnios, Dimitris,Kokotos, Christoforos G.
, p. 4451 - 4456 (2017)
Selective C-H activation is an area of growing importance in modern organic chemistry. Herein, we report our efforts in combining organocatalysis and photocatalysis for the development of a highly efficient and selective visible-light mediated protocol for the C-H activation and addition of various alcohols to a plethora of Michael acceptors, followed by a cyclization reaction leading to lactones, a repeatedly occurring motif in nature. Utilizing phenylglyoxylic acid as the photocatalyst and common household bulbs as the light source, we describe a versatile α-alkylation/lactonization of alcohols with α,β-unsaturated esters leading to products in excellent yields. The reaction mechanism was extensively studied.
Chemoenzymatic synthesis of enantioenriched 5-oxo-tetrahydro-3- furancarboxylic acid derivatives
Comini, Andrea,Forzato, Cristina,Nitti, Patrizia,Pitacco, Giuliana,Valentin, Ennio
, p. 617 - 625 (2007/10/03)
(R)-(+)-Paraconic acid 4, (S)-(-)-terebic acid 6 and their corresponding methyl and ethyl esters having ee's ranging from 60% to 92% were obtained by enzymatic resolution of their racemates. The enzymatic resolution of racemic ethyl γ-methylparaconates 14a and 14b allowed the isolation of the unreacted ester (2R,3R)-(+)-14a and that of the lactonic acid (2S,3R)-(-)-5b with 80% and 93% ee, respectively, the former by the use of Horse liver acetone powder (HLAP), the latter using α-chymotrypsin (α-CT). The enantiomeric ethyl (2S,3S)-(-)-14a and (2S,3R)-(-)-14b, both with >99% ee, were obtained by baker's yeast reduction of diethyl acetylsuccinate.
