Asymmetric Organocatalysed Synthesis of (R)‐Mandelic Acid Esters and α‐Alkoxy Derivatives from Commercial Sources DOI Creative Commons
Vincenzo Battaglia, Sara Meninno, Alessandra Lattanzi

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 11, 2024

Optically active mandelic acid esters represent a highly valuable class of building blocks in organic synthesis and recurrent motifs embedded bioactive compounds drugs. Herein, we provide an enantioselective one-pot based on Knoevenagel condensation/asymmetric epoxidation/domino ring-opening hydrolysis (DROH) sequence to the crude acids, which underwent final esterification step (R)-methyl mandelates. These products have been obtained good high overall yield enantioselectivity, using commercially widely available reagents catalyst including aldehydes, phenylsulfonyl acetonitrile, cumyl hydroperoxide, water epi-quinine-derived urea as organocatalyst. Moreover, versatility process has demonstrated prepare corresponding α-alkoxy manner, when primary alcohols domino (DROE) step. This system is first example non-enzymatic catalytic protocol allows straightforward asymmetric derivatives from aldehyde feedstocks.

Язык: Английский

Asymmetric Organocatalysed Synthesis of (R)‐Mandelic Acid Esters and α‐Alkoxy Derivatives from Commercial Sources DOI Creative Commons
Vincenzo Battaglia, Sara Meninno, Alessandra Lattanzi

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 11, 2024

Optically active mandelic acid esters represent a highly valuable class of building blocks in organic synthesis and recurrent motifs embedded bioactive compounds drugs. Herein, we provide an enantioselective one-pot based on Knoevenagel condensation/asymmetric epoxidation/domino ring-opening hydrolysis (DROH) sequence to the crude acids, which underwent final esterification step (R)-methyl mandelates. These products have been obtained good high overall yield enantioselectivity, using commercially widely available reagents catalyst including aldehydes, phenylsulfonyl acetonitrile, cumyl hydroperoxide, water epi-quinine-derived urea as organocatalyst. Moreover, versatility process has demonstrated prepare corresponding α-alkoxy manner, when primary alcohols domino (DROE) step. This system is first example non-enzymatic catalytic protocol allows straightforward asymmetric derivatives from aldehyde feedstocks.

Язык: Английский

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