Asymmetric synthesis of 2-azabicyclo[3.3.1]nonanes by a microwave-assisted organocatalysed tandem desymmetrisation and intramolecular aldolisation.
The six-membered nitrogen-containing ring of the morphan scaffold, ubiquitous in natural products, is formed by an intramolecular aldol process of an aza-tethered dicarbonyl compound, leading to the first asymmetric synthesis of a morphan derivative using organocatalysis.
Diaba
Faïza
F
Laboratori de Química Orgànica, Facultat de Farmàcia, Institut de Biomedicina, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain. faiza.diaba@ub.edu
Bonjoch
Josep
J
D000447:Aldehydes / Q000737:chemistry*; D053961:Azabicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008872:Microwaves; D011392:Proline / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D000447:Aldehydes; D053961:Azabicyclo Compounds; D007659:Ketones; C015662:2-aminoacetaldehyde; C116609:3-hydroxybutanal; D011392:Proline; D005998:Glycine