53912-83-7Relevant articles and documents
Synthesis of 2-Fluoroalkyl 4-Substituted Azepanes
Masson, Guillaume,Rioton, Sarah,Gomez Pardo, Domingo,Cossy, Janine
, p. 5497 - 5507 (2019/09/06)
Synthesis of di- and tri-substituted fluoroalkylated azepanes was achieved by ring expansion of pyrrolidines via a regioselective attack of nucleophiles on a bicyclic azetidinium intermediate. A broad scope of azepanes, substituted at C4 and bearing a α-t
Practical method for the synthesis of (R)-homopipecolinic acid and (R)-homoproline esters from ω-chloroalkanoic acids and available chiral amines
Hashimoto, Norio,Funatomi, Takashi,Misaki, Tomonori,Tanabe, Yoo
, p. 2214 - 2223 (2007/10/03)
A practical synthesis of (R)-homopipecolinic acid methyl ester 1 and (R)-homoproline methyl ester 2 was performed utilizing (i) a direct intramolecular cyclization of ω-chloro-β-enamino esters 11 and 12, which were prepared from available (S)-1-phenylethy
Studies towards the preparation of sparteine-like diamines for asymmetric synthesis
Harrison, Justin R.,O'Brien, Peter,Porter, David W.,Smith, Neil M.
, p. 3623 - 3631 (2007/10/03)
A route for the preparation of sparteine-like diamines starting from naturally occurring amino acids has been explored. Starting from the amino acids (S)-proline and (S)-phenylalanine, two novel sparteine-like diamines 2 and 3 have been prepared. The synthetic route involves Dieckmann condensation followed by a double Mannich reaction to set up the tricyclic structure with control of the relative stereochemistry. During the Dieckmann and Mannich reactions it was found that racemisation occurred either via retro-Michael or retro-Mannich processes. Conditions for preventing racemisation in the Dieckmann reaction were uncovered but it was not possible to prevent racemisation during the double Mannich reaction. Thus, the two novel sparteine-like diamines 2 and 3 have been prepared in racemic form. The Royal Society of Chemistry 1999.
