15190-13-3Relevant articles and documents
Straightforward α-Amino Nitrile Synthesis Through Mo(CO)6-Catalyzed Reductive Functionalization of Carboxamides
Trillo, Paz,Slagbrand, Tove,Adolfsson, Hans
, p. 12347 - 12351 (2018/09/10)
The selective reduction of amides into an intermediate hemiaminal catalyzed by Mo(CO)6 together with the inexpensive and easy to handle TMDS (1,1,3,3-tetramethyldisiloxane) as reducing agent, followed by subsequent trapping of the hemiaminal with a cyanide source, allows for the straightforward synthesis of α-amino nitriles. The methodology presented here, displays high levels of chemoselectivity allowing for the reduction of amides in the presence of functional groups such as ketones, imines, aldehydes, and acids, which affords a simple route for the synthesis of α-amino nitriles with a broad scope of functionalities in high yields. Furthermore, the applicability of this methodology is demonstrated by scale up experiments and by derivatization of the target compounds into synthetically interesting products. The selective cyanation is successfully applied in late stage functionalizations of amide containing drugs and prolinol derivatives.
A fast and benign synthesis of α-aminonitriles by reusable immobilized AlCl3on γ-Al2O3
Pamar, M. Geeta,Govender,Pillay,Abrahamse,Nanjundaswamy
, p. 110 - 116 (2015/01/30)
Reusable, immobilized AlCl3 on γ-Al2O3 is generated by the reaction of AlCl3 on activated γ-Al2O3 of 58 A at 600°C. This is an efficient, catalytic, safe and environmentally acceptable catalyst for the synthesis of a series of α-aminonitriles utilizing Strecker's process by the reaction of carbonyl compounds, amines and trimethylsilyl cyanide (TMSCN) with excellent yields at ambient temperature. The catalyst can be easily recycled and has been reused for thirteen runs without losing its activity.
Chirally deuterated benzyl chlorides from benzyl alcohols via hexachloroacetone/polymer-supported triphenylphosphine: Synthesis of protected (2S, 3S)-[3-2H, 15N]-tyrosine
Barnett, Derek W.,Refaei, Maryanne S.,Curley Jr., Robert W.
, p. 6 - 11 (2013/03/28)
Chirally deuterated benzyl chlorides were prepared using novel, general hexachloroacetone/polymer-supported triphenylphosphine treatment of chirally deuterated benzyl alcohols. Doubly labeled protected tyrosine was obtained in 62% yield with 86% de at the α-carbon and 82% de at the β-carbon. Key in the synthesis was the alkylation of 15N-labeled (-)-8-phenylmenthylhippurate with R-(-)-4-triisopropylsilyloxybenzyl-α-d chloride. Chirally deuterated benzyl chlorides were prepared in high yield with inversion from benzyl alcohols using solid-phase methods. One of the benzyl chlorides obtained was used in the synthesis of protected tyrosine labeled with 15N and chirally deuterated on the β-position. Copyright
