ISSN:
0947-3440
Keywords:
Asymmetric Strecker synthesis
;
α-Amino nitriles
;
Homochiral cyclic α-amino acids
;
Kinetic or thermodynamic control
;
Solvent effects
;
Optical rotation increments
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of the four 1-amino-2-methylcyclohexanecarboxylic acids 13, 14, 15, and 16 from diastereomeric mixtures of the α-amino nitriles 1-4 by successive application of conc. H2SO4, Pd/C H2, and conc. HCl is described. The amino nitriles 1-4 were prepared by asymmetric Strecker synthesis under various reactions, The formation of 1-4 is thermodynamically controlled in protic solvents (e.g. MeOH), whereas the reaction is under kinetic control in non-protic solvents (e.g. hexane), The separation of the α-amino amides 5-8, which were obtained by partial hydrolysis of 1-4, was achieved by CC, LPLC, and HPLC. The absolute configuration of all synthesized compounds was determined by means of only two X-ray analyses with consecutive correlations. The steric control of the asymmetric Strecker synthesis is discussed.
Additional Material:
8 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199619961126
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