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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
 
 

Synthesis of new chiral sulfinyldiacetic acid derivatives and attempt at chemoselective asymmetric Pummerer reaction.

(R(S))-1 (85% ee) was prepared by utilizing a porcin pancreatic lipase-promoted hydrolysis of sulfinyldiacetic acid dimethyl ester (8) which was derived from thiodiacetic acid (7). (R(S))-1 (99% ee) and (S(S))-1 (99% ee) were readily obtained by methanolysis of (R(S),S)-12 and (S(S),S)-12 with MeONa in MeOH. (R(S),S)-12 and (S(S),S)-12 were furnished by chromatographic separation of the diastereomeric mixture, obtained by oxidation of thiodiacetic mono-carboxylic acid (11) with 30% H2O2 followed by dehydrative condensation of the resultant sulfinyldiacetic mono-carboxylic acid with 4(S)-isopropyl-1,3-thiazolidine-2-thione. (R(S))-1 (99% ee) was successively treated with (TMS)2NLi, Ac2O, and TMSOTf to give a major chiral-3 product in 75% ee and in a highly chemoselective manner (chiral-3:chiral-2=93:7).[1]

References

  1. Synthesis of new chiral sulfinyldiacetic acid derivatives and attempt at chemoselective asymmetric Pummerer reaction. Nagao, Y., Miyamoto, S., Hayashi, K., Mihira, A., Sano, S. Chem. Pharm. Bull. (2002) [Pubmed]
 
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