The Preparation of Optically Active β-Keto Sulfoxides by Means of an Enantiomer-differentiating Reaction of α-Lithio Aryl Methyl Sulfoxides with Chiral Carboxylates

Abstract

Die Reaktion von entsprechenden Lithioarylmethylsulfoxiden (I) (aus dem entsprechenden Methylsulfoxid mit Li‐diethylamid) mit optisch aktiven Estern wie (II) verläuft enantioselektiv unter Bildung vontoptisch aktiven β‐Keto‐sulfoxiden wie (III) und entsprechenden Arylmethylsulfoxiden (IV) mit umgekehrter Konfiguration.

An Extremely Powerful Acylation Reaction of Alcohols with Acid Anhydrides Catalyzed by Trimethylsilyl Trifluoromethanesulfonate

“…After stirring for 21 h, the starting material (35) was consumed, and the mixture of products was 88:12 monoacetate (37):diacetate (38), and after a total of 3.5 days the ratio improved further to 93:7. Clearly, an equilibrium reaction was set up which eventually provided the thermodynamic product with the acetate group ending up on the alcohol group.…”

Scandium Trifluoromethanesulfonate as an Extremely Active Lewis Acid Catalyst in Acylation of Alcohols with Acid Anhydrides and Mixed Anhydrides

“…(1 S ,3 R ,5 S )-5-Methyl-2-(1-methylethyl)cyclohexyl 2,2-dimethylpropanoate (Table , entry 5): 1 H NMR (CDCl 3 , 300 MHz) δ 0.75 (d, J = 7.0 Hz, 3H), 0.80−1.11 (m, 3H), 0.89 (d, J = 6.8 Hz, 3H), 0.90 (d, J = 6.8 Hz, 3H), 1.19 (s, 9H), 1.30−1.44 (m, 1H), 1.44−1.56 (m, 1H), 1.62−1.72 (m, 2H), 1.82−2.00 (m, 2H), 4.62 (dt, J = 4.4, 10.8 Hz, 1H).…”

Visible light organophotoredox catalysis: a general approach to β-keto sulfoxidation of alkenes

“…All the products are known compounds and were characterized by comparison of their spectral data with those reported in the literature. 16,[21][22][23][28][29][30][31] Compound 3a. 28 Yellowish solid, m.p.…”