Stereoselective α-aminoallylation of aldehydes with chiral tert-butanesulfinamides and allyl bromides.
The combination of an aldehyde, an allylic bromide, and tert-butanesulfinamide in the presence of indium metal and titanium tetraethoxide allows straightforward access to homoallylamine derivatives in high yields and stereoselectivities. Moreover, the synthetic utility of the enantioenriched homoallylamine derived from n-decanal was illustrated in a concise synthesis of (+)-isosolenopsin. In this context, similar homoallylamines has been recently used by other groups in the synthesis of naturally occurring alkaloids.
González-Gómez
José C
JC
Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain. josecarlos.gonzalez@ua.es
Medjahdi
Mohamed
M
Foubelo
Francisco
F
Yus
Miguel
M
D000447:Aldehydes / Q000737:chemistry*; D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D000499:Allylamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002073:Butanes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
D000447:Aldehydes; D000498:Allyl Compounds; D002073:Butanes; D013449:Sulfonamides; C511422:tert-butanesulfinamide; D000499:Allylamine; C050431:allyl bromide