61861-00-5Relevant academic research and scientific papers
Convenient Access to Primary Amines by Employing the Barbier-Type Reaction of N-(Trimethylsilyl)imines Derived from Aromatic and Aliphatic Aldehydes
Gyenes, Ferenc,Bergmann, Kathryn E.,Welch, John T.
, p. 2824 - 2828 (1998)
A new versatile preparation of primary amines via benzylation of aromatic and aliphatic aldimines is described. Sonochemical and traditional methods for generation of the reactive intermediates are compared and contrasted. Competitive reactions were analyzed via free energy relationships to support the proposed alkylative mechanism.
Enantio- and Diastereoselective Synthesis of 1,5-syn-(Z)-Amino Alcohols via Imine Double Allylboration: Synthesis of trans-1,2,3,6-Tetrahydropyridines and Total Synthesis of Andrachcine
Allais, Christophe,Roush, William R.
supporting information, p. 2646 - 2649 (2017/05/24)
A stereoselective synthesis of trans-1,2,3,6-tetrahydropyridines 8 is described. This synthesis proceeds via intramolecular Mistunobu reactions of 1,5-syn-(Z)-amino alcohols 7, which were prepared by a highly diastereo- and enantioselective double-allylboration reaction of aldehyde 5 and silylimine 6. The chiral bifunctional γ-borylallylborane 9E was generated in situ by hydroboration of allene 3 with (diisopinocampheyl)borane 4. This strategy was applied to the total synthesis of andrachcine 1, thus establishing with certainty the absolute and relative configuration of the natural product.
STUDIES ON N-METALLO IMINES: SYNTHESIS OF N-UNSUBSTITUTED AZIRIDINES FROM N-TRIMETHYLSILYL IMINES AND LITHIUM ENOLATES OF α-HALO ESTERS.
Cainelli, Gianfranco,Panunzio, Mauro,Giacomini, Daria
, p. 121 - 124 (2007/10/02)
Addition of lithium enolates of 2-halo carboxylic esters to N-trimethylsilyl imines results in the formation of 1H-aziridine derivatives, in the Darzens fashion, with high cis-selectivity.
