Umpolung Reactivity of Aldehydes toward Carbon Dioxide

TY - JOUR

T1 - Umpolung Reactivity of Aldehydes toward Carbon Dioxide

AU - Juhl, Martin

AU - Lee, Ji-Woong

N1 - doi: 10.1002/anie.201806569

PY - 2018/9/17

Y1 - 2018/9/17

N2 - Carbon dioxide is an intrinsically stable molecule. Therefore, its activation requires extra energy input in the form of reactive reagents and/or activated catalysts and, often, harsh reaction conditions. Reported here is a direct carboxylation reaction of aromatic aldehydes with carbon dioxide to afford α-keto acids as added-value products. In situ generation of a reactive cyanohydrin was the key to the successful carboxylation reaction under operationally mild reaction conditions (25–40 °C, 1 atm CO2). The resulting α-keto acids served as a platform for α-amino acid synthesis by reductive amination reactions, illustrating the chemical synthesis of essential bioactive molecules from carbon dioxide.

AB - Carbon dioxide is an intrinsically stable molecule. Therefore, its activation requires extra energy input in the form of reactive reagents and/or activated catalysts and, often, harsh reaction conditions. Reported here is a direct carboxylation reaction of aromatic aldehydes with carbon dioxide to afford α-keto acids as added-value products. In situ generation of a reactive cyanohydrin was the key to the successful carboxylation reaction under operationally mild reaction conditions (25–40 °C, 1 atm CO2). The resulting α-keto acids served as a platform for α-amino acid synthesis by reductive amination reactions, illustrating the chemical synthesis of essential bioactive molecules from carbon dioxide.

KW - amino acids

KW - carbon dioxide fixation

KW - carboxylation

KW - reaction mechanisms

KW - umpolung

U2 - 10.1002/anie.201806569

DO - 10.1002/anie.201806569

M3 - Journal article

C2 - 30035859

SN - 1433-7851

VL - 57

SP - 12318

EP - 12322

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 38

ER -