Synthesis of α-Hydroxy Aldehyde and α-Hydroxy Acid Derivatives fromβ-Hydroxy orβ-Oxo Sulfoxides

Abstract

A method for the conversion of allyl alcohol into glyceraldehyde derivatives by the cooxidation with thiol by oxygen and the successive Pummerer reaction is described. Several methods to transform ti-hydroxy or ti-oxo sulfoxides into "activated ester forms" of a-hydroxy acids are reported. By these methods, derivatives of mandelic acid and lactic acid were prepared from 2-hydroxy-2-phenylethyl p-tolyl sulfoxide and phenylsulfinylacetone, respectively. From a derivative of !'i-alanine were prepared some derivatives of 4-amino-2-hydroxybutyric acid which is used for the modification of aminoglycoside antibiotics.

Synthesis of β‐Keto Sulfoxides via Copper(II)‐Catalyzed Aerobic Oxidation

“…To further verify the application properties of this kind of compound, a series of derivatization reactions on the obtained β ‐keto sulfoxide 3 a were performed according to previous literature, and the corresponding products were obtained with satisfied yields (Scheme 5). [3b,11–13] For example, 3 a reacted with Ac 2 O in the presence of pyridine or direct treated with HCl under H 2 O/DMSO to give thioester 4 and 5 with 95% and 80% yield respectively. And 3 a can also react with MeOH to give α ‐keto acetal 6 via I 2 catalysis.…”