Chiral Brønsted acid catalyzed asymmetric oxidation of N-acyl sulfenamide by H2 O2 : An efficient approach to obtaining chiral N-acyl sulfinamide.
Chirality
; 34(9): 1191-1196, 2022 09.
Article
em En
| MEDLINE
| ID: mdl-35681267
ABSTRACT
Although the power of chiral sulfinamide reagents in synthetic chemistry has long been recognized, methods for their synthesis are still auxiliary-based approaches which possess the disadvantages of poor atom economy and limited substrate universality. Due to the weak nucleophilicity of amides, it is more difficult to prepare chiral N-acylsulfinamides by traditional methods. Herein, we describe an example of catalytic asymmetric synthesis of N-acyl sulfinamides. In this work, N-acyl sulfenamides act as useful substrates, because of the indispensable N-H bond, which could form an efficient hydrogen bond with chiral phosphoric acid. H2 O2 (35%) was used as the terminal oxidant for preparation of sulfinamides in high yields and enantioselectivities, which could be easily derivatized to sulfoxides without loss of the enantioselectivity.
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Base de dados:
MEDLINE
Assunto principal:
Sulfamerazina
/
Amidas
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article