Method for synthesizing chiral sulfenamide

Abstract

The invention discloses a method for synthesizing chiral sulfonamide. In the method, chiral thiosulfinate is taken as a raw material and reduced with liquid ammonia containing lithium amide to obtain the chiral sulfonamide, and a reaction formula is as above, wherein, R is one of C1-C10 alkyl, phenyl, p-cresyl, o-cresyl, metal-cresyl, p-ethyl benzyl, p-tertiary-butyl phenyl, p-acetyl phenyl, o-acetyl phenyl and naphthyl. The method sequentially comprises the following steps: preparing the lithium amide; dropwise adding the lithium amide to chiral thiosulfinate solution and stirring for reaction; and adding ice to obtained mixture after the reaction, extracting, combining organic phases and eliminating solvents, and crystallizing to obtain the chiral sulfonamide. The method has the advantages that synthesis cost is reduced by an oxidation method in the presence of a chiral catalyst; a ligand is a condensation product of cheap and available chloromycetin derivative and salicylaldehyde derivative; and reaction steps are less, the reaction conditions are mild and post-treatment is simple.

Description

technical field [0001] The invention relates to a method for synthesizing chiral sulfinamides, and relates to a method for preparing chiral sulfinamides by using chiral ligands and metal catalysts to catalyze asymmetric oxidation and reductive amination of lithium amide. Background technique [0002] Chiral alkyl (aryl) sulfinamides have important application significance in the fine organic synthesis and the synthesis of chiral drugs. Using it as a chiral prosthetic group can asymmetrically synthesize many chiral amine compounds and many chiral drugs that are difficult to synthesize by common routes (Jonathan, A.Ellman; Timothy, D.Owens and Tony, P.Tang Account Chemical Research 2002 , 35, 984-995). [0003] And the common preparation method of chiral alkyl (aryl) sulfinamide has following several: one, is to utilize the method for chiral prosthetic group to prepare, and the method published in 2002 with Chris H.Senanayake etc. is its representative ( Zhengxu, Han; Dhilee...

AI Technical Summary

Problems solved by technology

This method has a long route, and the cost is very high due to the use of equivalent chiral prosthetic groups; although the chiral prosthetic group may be recycled, the route is cumbersome and greatly increases the cost of this route. The reaction formula is:

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