C-alkylations and C-C bond formation.via alkyl halide, PTC & Schiff base deriv. of monoalkyl amino acids.
Summary (of (1) to (10): C-alkylation of (Subst.) Benzyl halide via an amino acid (such as alanine or glycine, etc.). to give the corresponding benzyl-alanine, benzyl-glycine, which can, subsequently be decarboxylated to give a phenethylamine. (analogous reactions could also work to give tryptamines).
1) Sterically Controlled Synth of alpha-methyldopa, Chem. & Ind. 1972, 687-688.
Synthesis of amino acids.
2) The Synth. of amino acids by PTC. (O'Donnell & Co). TL 30 (1978), 2641-2644.
3) Alkylation of aldimine and ketimine derivs. of glycine ethyl ester under PTC.; TL 23, #41 (1982), 4255-4258. Martin O'Donnell & Co.
4) alpha-amino acids by PTC.; TL 23, #41 (1982), 4259-4262. Martin O'Donnell & Co. Abstract: alpha-amino acids, alpha-methyl p-chlorophenylalanine, alpha-methyl p-tyrosine, alpha-methyl m-tyrosine and alpha-methyl DOPA have been prepared in good yields from amino ester hydrochlorides. The key step is the PTC alkylation of Schiff base deriv. of monoalkyl amino acids.
5) alpha-alkylation of amino acids without racemization. Prepn. of either (S)- or (R)- alpha-methyl DOPA from (S)-alanine. Helv. Chim. Acta 68 (1985), 144-154.
6) Amino acids & Peptides. XXVIII. A New Synth. of alpha-amino acid derivs. by alkylation of Schiff bases derived from Glycine & Alanine. Chem. Pharm. Bull. 25(9) 2287-2291 (1977).
7) Liebigs Ann. Chem. 1981, 696-708 (German); Asymmetrische Synthese von alpha-Methylaminosauren durch Alkylieren des lithiierten Lactimethers van cyclo-(L-Ala-L-Ala)
The Synth. of amino acid derivs. by PTC alkylations. TL 47 (1978), 4625-4628.
9) Alkylation of protected alpha-amino acid derivs. in the presence of Pot. Carb. Synthesis April 1984, 313-315.
10) Microwave irradiated Alkylations of Active methylenes under solid-liquid PTC conditions. Y Jiang, Y Wang, R Deng & A Mi; From Phase-Transer Catalysis (Chapter 16), Ed. Marc Halpern, ISBN: 0841234914.
Darzens & variants.11) Reactions of Organic anions. XLIII. Catalytic method for synth. of Glycidic nitriles in aq. medium. TL 23 (1972), 2395-2396.
12) Stereochemical control of interfacial Darzens Condensation. JCS Chem. Comm. 1977, 902-903.
13) Two Phase Darzens Condensation Rxn with Octopus Cpds as a Catalyst. Bull. Chem. Soc. Jpn. 53 (1980), 1463-1464.
Whatever14) beta-2,5-dihydroxyphenyl-DL-alanine. Biochemical Preparations 3 (1953). 79-83.