Synthesis of α-Amino Acids and DerivativesRelated

Phase-transfer-catalyzed alkylation of glycinateSchiff base with racemic secondary alkylhalides proceeded with excellent levels of synandenantioselectivities under the influence of achiral quaternary ammonium bromide and 18-crown-6. The alkylation product can beselectively converted to the corresponding antiisomer, allowing the preparation of all thestereoisomers of β-alkyl-α-amino acidderivatives.
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Synthesis of α-Amino Acids and DerivativesRelated Synthesis of α-Amino Acids and DerivativesRelated:Name ReactionsPetasis ReactionRecent LiteratureDiethyl N-Boc-iminomalonate, prepared onmulti-gram scale, served as a stable and highlyreactive electrophilic glycine equivalent whichreacted with organomagnesium compoundsaffording substituted aryl N-Boc-aminomalonates. Subsequent hydrolysisproduced arylglycines.P. Cali, M. Begtrup, Synthesis, 2002, 63-64.Using a cinchonine-derived alkaloid catalyst,enantioselective alkylations of N-(diphenylmethylene) glycine tert-butyl esterwere efficiently carried out with various alkylhalides to give products in high enantiomericexcess.W. He, Q. Wang, Q. Wang, B. Zhang, X. Sun,S. Zhang, Synlett, 2009, 1311-1314.Phase-transfer-catalyzed alkylation of glycinateSchiff base with racemic secondary alkylhalides proceeded with excellent levels of syn-and enantioselectivities under the influence of achiral quaternary ammonium bromide and 18-crown-6. The alkylation product can beselectively converted to the corresponding antiisomer, allowing the preparation of all thestereoisomers of β-alkyl-α-amino acidderivatives.T. Ooi, D. Kato, K. Inamura, K. Ohmatsu, K.Maruoka, Org. Lett., 2007, 9, 3945-3948.A new method for the Rh(I)-catalyzed additionof arylboronic acids to chiral N-tert-butanesulfinyl imino esters allows theasymmetric synthesis of arylglycine derivativesin high yields and diastereoselectivities forvarious functionalized arylboronic acids.M. A. Beenen, D. J. Weix, J. A. Ellman, J. Am.Chem. Soc., 2006, 128, 6304-6305.A cationic palladium-complex catalyzes theaddition of arylboronic acids to N-tert-butanesulfinyl iminoacetates to yield opticallyactive arylglycine derivatives with good yieldand high diastereoselectivity. This reactionprovides a convenient and efficient method forthe synthesis of arylglycine derivatives.H. Dai, X. Lu, Org. Lett., 2007, 9, 3077-3080.An efficient method for the asymmetricsynthesis of anti-β-hydroxy-α-amino acidderivatives is based on highly enantio- anddiastereoselective aldol reactions of the siliconenolate derived from N-trifluoroacetylglycinatewith aldehydes using a chiral zirconiumcatalyst.J. Kobayashi, M. Nakamura, Y. Mori, Y.Yamashita, S. Kobayashi, J. Am. Chem. Soc.,2004, 126, 9192-9193.A highly efficient direct asymmetric aldolreaction of a glycinate Schiff base withaldehydes has been achieved under mildbiphasic conditions with excellentstereochemical control, using a chiral quaternaryammonium salt as a phase-transfer catalyst.T. Ooi, M. Kameda, M. Taniguchi, K. Maruoka,J. Am. Chem. Soc., 2004, 126, 9685-9694.A copper(I)-catalyzed direct three-componentcoupling of ethyl glyoxylate, p-anisidine, andterminal alkynes provides β,γ-alkynyl α-aminoacid derivatives in good yields.Z. Shao, A. S. C. Chan, Synthesis, 2008, 2868-2870.The regioselective opening of Bn2N-α-methylserine-β-lactone with organocupratesgave enantiopure α-methyl amino acids inexcellent yields.N. D. Smith, A. M. Wohlrab, M. Goodman,Org. Lett., 2005, 7, 255-258.In the presence of a catalytic amount ofCu(OTf)2 and a chiral diamine ligand, variousN-acylimino esters reacted smoothly with silylenol ethers and alkyl vinyl ethers to afford thecorresponding Mannich-type adducts in highyields with high diastereo- andenantioselectivities. The reaction mechanism isdiscussed.S. Kobayashi, R. Matsubara, Y. Nakamura, H.Kitagawa, M. Sugiura, J. Am. Chem. Soc., 2003,125, 2507-2515.Both (3R,5R)-5-methyl-3-pyrrolidinecarboxylicacid and (R)-3-pyrrolidinecarboxylic acidefficiently catalyzed the Mannich-type reactionsof aldehydes with α-imino esters under mildconditions and afforded anti-Mannich productswith high diastereo- and enantioselectivities.H. Zhang, S. Mitsumori, N. Utsumi, M. Imia, N.Garcia-Delgado, M. Mifsud, K. Albertshofer, P.H.-Y. Cheong, K. N. Houk, F. Tanaka, C. F.Barbas, III, J. Am. Chem. Soc., 2008, 130, 875-886.Direct catalytic, enantioselective, anti-selectiveMannich-type reactions between unmodifiedketones and α-imino esters using 5-10 mol % of(R)-3-pyrrolidinecarboxylic or (R)-β-proline ascatalyst in 2-PrOH at room temperature gaveproducts in good yields with high diastereo- andenantioselectivities.H. Zhang, M. Mifsud, F. Tanaka, C. F. Barbas,III, J. Am. Chem. Soc., 2006, 128, 9630-9631.Proline-catalyzed Mannich-type reactions of N-PMP-protected α-imino ethyl glyoxylate with avariety of unmodified ketones providedfunctionalized α-amino acids in high yields withexcellent regio-, diastereo-, andenantioselectivities. In reactions involvingketone donors where diastereoisomeric productscould be formed, two adjacent stereogeniccenters were created simultaneously uponcarbon-carbon bond formation with completesyn-stereocontrol.A. Cordova, W. Notz, G. Zhong, J. M.Betancort, C. F. Barbas, J. Am. Chem. Soc.,2002, 124, 1842-1843.Proline-catalyzed Mannich-type reactions of N-PMP-protected α-imino ethyl glyoxylate with avariety of unmodified aliphatic aldehydesprovided functionalized α-amino acids in highyields with excellent enantioselectivities. Thediastereoselectivity of the reaction increasedwith the bulkiness of the substituents of thealdehyde donor.A. Cordova, W. Notz, G. Zhong, J. M.Betancort, C. F. Barbas, J. Am. Chem. Soc.,2002, 124, 1866-1867.A direct highly anti-selective andenantioselective asymmetric Mannich reactionusing a novel axially chiral aminotrifluoromethanesulfonamide has beendeveloped. Reactions between aldehydes and N-PMP-protected α-imino ethyl glyoxylateproceed smoothly to give β-amino aldehydeswith high anti/syn ratio and enantioselectivity.T. Kano, Y. Yamaguchi, O. Tokuda, K.Maruoka, J. Am. Chem. Soc., 2005, 127, 16408-16409.(3R,5R)-5-methyl-3-pyrrolidinecarboxylic acidas catalyst for Mannich-type reaction ...