Synthesis of dihydropyrano[4,3-b]pyranes via a multi-component reaction catalyzed by lipase

Abstract

A green method for the synthesis of dihydropyrano[4,3-b]pyranes via a three-component reaction catalyzed by lipase is reported firstly. Under the optimal conditions, high yields of dihydropyrano [4,3-b]pyranes (80.8-96.8%) could be obtained in this enzymatic reaction. This study not only expands the application of lipase in organic synthesis, but also provides an alternative efficient method for the synthesis of dihydropyrano[4,3-b]pyranes.

Hemoglobin: A New Biocatalyst for the Synthesis of 2‐substituted Benzoxazoles via Oxidative Cyclization

“…Biocatalysis is an important tool used in environmentally friendly and sustainable processes for the synthesis of organic molecules . Mining for new types of organic reactions that can be catalyzed by proteins has drawn much attention in recent years and has dramatically expanded the application of proteins within the field of organic chemistry . Hemoproteins are promising biocatalysts for synthetic applications that incorporate oxidative reactions (hydroxylation, epoxidation, and sulfoxidation) and carbene‐mediated transformations (olefin cyclopropanation, carbene insertion, and aldehyde olefination) .…”

“…[11] Mining for new types of organic reactions that can be catalyzed by proteins has drawn much attention in recent years and has dramatically expanded the application of proteins within the field of organic chemistry. [12][13][14][15][16][17][18] Hemoproteins are promising biocatalysts for synthetic applications that incorporate oxidative reactions (hydroxylation, epoxidation, and sulfoxidation) and carbene-mediated transformations (olefin cyclopropanation, carbene insertion, and aldehyde olefination). [19][20][21][22][23][24][25] Hemoglobin, a necessary vehicle for oxygen transport in the body, has been also used in several organic reactions as a stable and abundant biocatalyst, such as lipid peroxidation, aniline hydroxylation, oxidation of hydrogen sulfide and pyrene.…”

Bio-Catalysis in Multicomponent Reactions

“…Several enzyme-catalyzed three-component “Hantzsch-type” reactions where the amine partner is replaced by malonitrile, giving rise to several pyran derivatives, have appeared as an alternative access to this important class of compounds under mild, efficient and environment-friendly conditions [ 55 , 56 , 57 ] ( Scheme 11 ).…”

Synthesis of functionalized 4H-Chromenes catalyzed by lipase immobilized on magnetic nanoparticles

“…Enzyme catalytic promiscuity is the ability of an enzyme active site to catalyze several different chemical transformations, such as Michael addition, aldol addition, Morita-Baylis-Hillman reaction, Knoevenagel reaction and perhydrolysis (6)(7)(8)(9)(10). Based on these findings, many enzymatic MCRs have been reported to generate complex bioactive molecules, and these researches have dramatically widened the application of enzyme catalytic promiscuity in synthetic chemistry (11)(12)(13)(14)(15). However, most of these enzymatic MCRs have encountered the problems of poor stability and difficulties in recovery and recycling for enzymes when these reactions were taken under the conditions far from their physiological environment.…”