3-Aminopyrrolidines via ring rearrangement of 2-aminomethylazetidines. Synthesis of (-)-absouline.
[reaction: see text] A new entry to enantiopure 3-aminopyrrolidines was developed using a boron trifluoride-mediated rearrangement of 2-aminomethylazetidines. The method is quite general and produces rearranged products in good yield regardless of both substitution pattern and relative stereochemistry of the starting material. A concise stereocontrolled synthesis of (-)-absouline was achieved on the basis of this new method.
Vargas-Sanchez
Monica
M
Laboratoire SIRCOB, UMR CNRS 8086, Université de Versailles Saint Quentin en Yvelines, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France.
Couty
François
F
Evano
Gwilherm
G
Prim
Damien
D
Marrot
Jérome
J
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001384:Azetidines / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D001384:Azetidines; D011759:Pyrrolidines; C513049:absouline