37929-85-4Relevant academic research and scientific papers
Efficient synthesis of tertiary amines from secondary amines
Kurosu, Michio,Dey, Sevendu Sekhar,Crick, Dean C.
, p. 4871 - 4875 (2007/10/03)
Reliable N-alkylations of secondary amines have been developed. By using DIAD and TPP (or PS-TPP) a variety of secondary amines can be converted to the corresponding tertiary amines in good to excellent yields with diverse alkylhalides; no formation of quaternary amine salts are observed. These protocols are amenable to combinatorial chemistry libraries, and are also useful for the syntheses of secondary amines by an acid lysis of the cleavable tertiary amino resins.
Tandem formation and [2,3] rearrangement of methylene ammonium ylides derived from amines and the Simmons-Smith reagent
Aggarwal, Varinder K.,Fang, Guang Yu,Charmant, Jonathan P. H.,Meek, Graham
, p. 1757 - 1760 (2007/10/03)
(Matrix presented) Zinc-complexed methylene ammonium ylides are formed from tertiary amines and the Simmons-Smith reagent. These stable entities can be activated with n-BuLi to allow reactions typical of ammonium ylides such as [2,3] rearrangements. In th
Synthesis of tertiary amines using a polystyrene (REM) resin
Brown, Angus R.,Rees, David C.,Rankovic, Zoran,Morphy, J. Richard
, p. 3288 - 3295 (2007/10/03)
A range of tertiary amines was constructed using a 'traceless' linker on a polystyrene resin (REM resin), starting from seconday amines, primary amines, and resin-bound 'ammonia'. The methodology is characterized by three essential steps conducted under ambient conditions: (1) coupling of the starting amine (Michael addition) to the resin, (2) activation (quaternization), and (3) cleavage of the product amine (Hofmann elimination). The linker is compatible with both acid and base sensitive protecting group strategies. The nature of the chemistry ensures that the tertiary amine products are obtained in consistently high purity (95% or greater). After cleavage of the product, REM resin is regenerated and can be reused for repeat syntheses. The yield and purity of repeat batches is maintained over 5 cycles, allowing the automated synthesis of >0.5 g quantities of pure tertiary amine.
A novel linker strategy for solid-phase synthesis
Morphy, J. Richard,Rankovic, Zoran,Rees, David C.
, p. 3209 - 3212 (2007/10/03)
The REM resin for solid phase synthesis is described. Its use is illustrated by preparing a small array of tertiary amines using a Hoffman elimination reaction. No functional group is required for linking these compounds onto the resin other than the amin
