Diastereoselective synthesis of bis(α-aminophosphonates) by lipase catalytic promiscuity

Abstract

New bis(α-aminophosphonates) were directly prepared with high diastereoselectivity by lipase catalytic promiscuity in the presence of immobilized Candida antarctica lipase.

Relationship between Structure and Antibacterial Activity of α-Aminophosphonate Derivatives Obtained via Lipase-Catalyzed Kabachnik−Fields Reaction

“…The Kabachnik–Fields reaction is the most efficient method for the formation of carbon−phosphorus bonds using an aldehyde, amine, and H -phosphite. A number of other synthetic approaches have also been reported for the preparation of α-aminophosphonates [ 7 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 , 85 , 86 , 87 , 88 , 89 , 90 , 91 , 92 , 93 , 94 , 95 ]. These methods are generally conducted in the presence of various organic and inorganic bases [ 56 , 57 , ...…”

“…Although some chemical strategies work towards the synthesis of α-aminophosphonates, the biocatalytic preparation of target α-aminophosphonates remains unexploited. It was shown that some selected α-aminophosphonates could be obtained from aniline derivatives by the Kabachnik–Fields reaction using Candida antarctica lipase B (CAL-B) as a catalyst [ 71 , 72 , 73 ].…”

“…All microorganisms and media were accurately described in detail in the previous work [ 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 ] and analyzed by a Tukey test.…”

Microbial Lipases and Their Potential in the Production of Pharmaceutical Building Blocks

“…In this sense, in the same research line, the enzymes from the previous study along with rabbit gastric lipase (RGL) were evaluated in the KF reaction using benzidine, diethylphosphite and several aldehydes in order to evaluate their diastereoselectivity in obtaining bis (α-aminophosphonates). CAL B immobilized in acrylic resin using THF as the solvent for 30 min and at 50 °C had a yield of 90% [ 217 ]. This enzyme derivative was reused for four cycles and in the last one, the yield was reduced to 69%.…”

“…As for diastereoselectivity (meso/DL ratio), it depended on aldehyde used (electronic effects), but in most cases it was high (71 to 100%). These values were maintained when the synthesis scale was raised to the multigram order [ 217 ].…”