- Enantioselective Synthesis of α-Substituted Serine Derivatives via Cu-Catalyzed Oxidative Desymmetrization of 2-Amino-1,3-diols
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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.
- Yamamoto, Kosuke,Ishimaru, Shota,Oyama, Tatsuya,Tanigawa, Satoko,Kuriyama, Masami,Onomura, Osamu
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p. 660 - 666
(2019/03/26)
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- Theoretical evidence for pyramidalized bicyclic serine enolates in highly diastereoselective alkylations
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A new chiral serine equivalent and its enantiomer have been synthesized from (S)- and (R)-N-Bocserine methyl esters (Boc: tert-butyloxy-carbonyl). The use of these compounds as chiral building blocks has been demonstrated in the synthesis of α-alkyl α-amino acids by diastereoselective po tassium enolate alkylation reactions and subsequent acid hydrolyses. Theoretical studies were performed to eluci date the stereochemical outcome of both the formation of five-membered cyclic N,O-acetals and the subsequent alkylation process, which occurs with total retention of configuration. This feature could be explained in terms of the high degree of pyramidalization of enolate intermediates.
- Aydillo, Carlos,Jimenez-Oses, Gonzalo,Busto, Jesus H.,Peregrina, Jesus M.,Zurbano, Maria M.,Avenoza, Alberto
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p. 4840 - 4848
(2008/02/04)
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- METHOD FOR PRODUCING ALPHA-METHYLATED CYSTEINE AND SERINE DERIVATIVES
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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.
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Page/Page column 30
(2008/06/13)
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- Synthesis of a new conformationally constrained glycoamino acid building block
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The synthesis of a suitably protected β-D-glucopyranosyl-(S)-α-methylserine derivative - a new conformationally constrained glycosylated quaternary amino acid analogue of β-D-glucopyranosyl-L-serine - is described. This compound can be used as an attractive building block for the synthesis of new, constrained glycopeptides.
- Avenoza, Alberto,Peregrina, Jesús M.,San Martín, Emilio
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p. 6413 - 6416
(2007/10/03)
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- Enantioselective synthesis of (S)- and (R)-α-methylserines: Application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals
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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.
- Avenoza, Alberto,Cativiela, Carlos,Corzana, Francisco,Peregrina, Jesus M.,Sucunza, David,Zurbano, Maria M.
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p. 949 - 957
(2007/10/03)
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