Regio- and stereoselective aminopentadienylation of carbonyl compounds.
A simple and robust protocol is detailed for the preparation of enantioenriched α-substituted (1,4-pentadien-3-yl)amine derivatives. The methodology involves the addition of an in situ formed pentadienyl indium reagent to chiral tert-butylsulfinimines, previously formed in the same pot. The addition takes place with excellent γ-regio- and diastereoselectivity for a wide range of carbonyl compounds, including α-unsubstituted aldehydes and methyl alkyl ketones. The catalytic hydrogenation of the sulfinamines obtained provides a convenient access to chiral α-substituted (3-pentyl)amines. The hydroboration-oxidation of the α-(1,4-pentadien-3-yl)amine derivatives, followed by a cyclization under Mitsunobu conditions, takes place with an excellent diastereoselectivity governed by the chiral sulfinyl group.
Departamento de Quı́mica Orgánica, Facultad de Ciencias and Instituto de Sı́ntesis Orgánica (ISO), Universidad de Alicante , Apdo. 99, 03080 Alicante, Spain.
Irene
I
Bosque
Emine
E
Bagdatli
Francisco
F
Foubelo
Jose C
JC
Gonzalez-Gomez