114396-62-2Relevant articles and documents
Enantioselective Synthesis of α-Substituted Serine Derivatives via Cu-Catalyzed Oxidative Desymmetrization of 2-Amino-1,3-diols
Yamamoto, Kosuke,Ishimaru, Shota,Oyama, Tatsuya,Tanigawa, Satoko,Kuriyama, Masami,Onomura, Osamu
, p. 660 - 666 (2019/03/26)
The enantioselective copper-catalyzed oxidative desymmetrization for the synthesis of chiral α-substituted serine derivatives is reported. The combination of Cu(OTf)2/(R,R)-PhBOX catalyst system, N-bromosuccinimide, and MeOH enables us to provide chiral α-substituted serines from N-2-methylbenzoyl-protected 2-amino-1,3-diols through a simple procedure at room temperature under an air atmosphere. A variety of α-substituent including aryl and heteroaryl groups were tolerated in this method, and the corresponding chiral serine derivatives were obtained in good to high yields with high enantioselectivities.
METHOD FOR PRODUCING ALPHA-METHYLATED CYSTEINE AND SERINE DERIVATIVES
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Page/Page column 30, (2008/06/13)
The invention relates to an improved method for the production, purification and crystallisation of alpha -methylated cysteine or serine derivatives by an acid hydrolysis of corresponding thiazolidine or oxazolidine esters, with the continuous removal of the accumulating aldehyde, a prior optional conversion into a thiazolidine or oxazolidine carboxylic acid or a thiazolidine or oxazolidine carboxylate and a subsequent azeotropic distillation.
Enantioselective synthesis of (S)- and (R)-α-methylserines: Application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals
Avenoza, Alberto,Cativiela, Carlos,Corzana, Francisco,Peregrina, Jesus M.,Sucunza, David,Zurbano, Maria M.
, p. 949 - 957 (2007/10/03)
This report describes the synthesis of enantiomerically pure (S)- and (R)-α-methylserines on a multigram scale, starting from the Weinreb amide of 2-methyl-2-propenoic acid and using a stereodivergent synthetic route that involves a Sharpless asymmetric dihydroxylation reaction. As a synthetic application of these quaternary α-amino acids, they were used as starting materials in the synthesis of the well-known valuable homochiral (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinal building blocks.