A sustainable innovation for the tandem synthesis of sugar-containing coumarin derivatives catalyzed by lipozyme TL IM fromThermomyces lanuginosusin continuous-flow microreactors

Abstract

We developed an efficient and environmentally friendly two-step tandem methodology for the synthesis of sugar-containing coumarin derivatives catalyzed by lipozyme TL IM from Thermomyces lanuginosus in continuous-flow microreactors. Compared to those observed for other methods, the salient features of this work including green reaction conditions, short residence time (50 min), and catalysts are more readily available and the biocatalysis reaction process is efficient and easy to control. This two-step tandem synthesis of coumarin derivatives using the continuous-flow technology is a proof of concept that opens the use of enzymatic microreactors in coumarin derivative biotransformations. a Reaction conditions: salicylaldehyde (1a) (50 mM), diethyl malonate (2a) (100 mM), catalysts in 5 mL solvent, at 50 C for 24 h. b Isolated yields.This journal is

Sugars in Multicomponent Reactions: A Toolbox for Diversity-Oriented Synthesis

“…Du, Luo, and co-workers 77 developed a protocol to synthesize a series of sugar-containing 2-oxo-1-benzopyran-3carboxylates 238 via a two-step tandem reaction of salicylaldehydes 234, dimethyl malonate (235, R 4 = Me), and sugar moieties 237 catalyzed by an enzyme, lipozyme TL IM (from Thermomyces lanuginosus) in a continuous-flow micro-reactor in good yields (up to 75%) (Scheme 61). This synthetic methodology is a better approach compared to other traditional methodologies in terms of greener approach, reaction time, enzyme as a catalyst, broad substrate scope, and high regioselectivity.…”