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Di-tert-butyl azodicarboxylate is a reagent used in the preparation of acyl hydrazinedicarboxylates. It is also used in the electrophilic amination of beta-keto esters catalyzed by an axially chiral guanidine. It serves as a precursor in an enantioselective synthesis of 3,6-dihyropyridazines employing organocatalysts such as L-proline or (S)-2-pyrrolidinyl tetrazole. It is also utilized in the asymmetric Friedel-Crafts amination through a chiral organocatalyst. Further, it acts as a reactant for preparation of hexapeptide key fragments through stereo selective selenocyclization/oxidative deselenylation reactions. In addition to this, it is employed as a starting material in the synthesis of pyrroloisoquinoline template through stereoselective N-acyliminium-mediated cyclization and enolate amination for preparation of peptidomimetic compounds and Barbier-type propargylation reactions.
Aza-dienophile. The ester groups are readily removed from adducts by acid: J. Org. Chem., 26, 4336 (1961); 38, 2043 (1973); 40, 563 (1975).
Useful "NH2 +" synthon for enantioselective amination reactions: J. Am. Chem. Soc., 108, 6394, 6395, 6397 (1986); Tetrahedron Lett., 29, 6765 (1988).
Mitsunobu reaction with alcohols gives a direct route to the corresponding N,N'-di-Boc protected hydrazine derivatives: Tetrahedron Lett., 37, 4327 (1996).
Kasaplar, P.; Ozkal, E.; Rodríguez-Escrich, C.; Pericàs, M. A. Enantioselective alpha-amination of 1,3-dicarbonyl compounds in batch and flow with immobilized thiourea organocatalysts. Green Chem. 2015, 17 (5), 3122-3129.
Yang, X.; Toste, F. D. Direct Asymmetric Amination of alpha-Branched Cyclic Ketones Catalyzed by a Chiral Phosphoric Acid. J. Am. Chem. Soc. 2015, 137 (9), 3205-3208.
Hazard Statements: H228-H315-H319-H335
Flammable solid. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P240-P241-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P362-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant