22813-61-2Relevant articles and documents
The efficient preparation of α, β, γ-lactam derivatives
Lee, Mi-Jee,Jang, Ji-Sung,Ahn, Chuljin
, p. 855 - 858 (2014/02/14)
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Trimethylaluminium mediated amide bond formation in a continuous flow microreactor as key to the synthesis of rimonabant and efaproxiral
Gustafsson, Tomas,Ponten, Fritiof,Seeberger, Peter H.
, p. 1100 - 1102 (2008/09/21)
A safe, functional-group-tolerant and high-throughput version of the trimethylaluminium mediated amide bond formation reaction has been developed in a microreactor system; rimonabant and efaproxiral were prepared to illustrate the utility of the method. The Royal Society of Chemistry.
Preparation and reactivity of chiral β-amino-alkylzinc iodides and related configurationally stable zinc organometallics
Duddu,Eckhardt,Furlong,Knoess,Berger,Knochel
, p. 2415 - 2432 (2007/10/02)
Several zinc organometallics bearing at the β-position a carbamate or an amido function with an acidic N-H group were prepared using the direct insertion of zinc dust into the corresponding alkyl iodides in THF or THF:DMSO mixtures. Most of the starting iodides were obtained from natural α-amino acids and the resulting zinc species afforded after transmetalation with CuCN.2LiCl and reaction with a selection of relatively reactive electrophiles a variety of polyfunctional 1,2-amino alcohol derivatives and carbamates in optically pure form. Several secondary β-amido alkyl iodides were converted to the corresponding chiral zinc reagents and trapped with electrophiles. The configurational stability of chiral secondary organozinc compounds and the stereochemical course of their reactions were examined.