One-pot tandem double-aldol reaction/aza-addition of acetylacetamides and o-phthalaldehyde leading to spiroindan-2,2'-pyrrolidines.
A novel domino reaction based on o-phthalaldehyde and 3-oxo-N-arylbutanamide 1 has been developed which allows one-pot and efficient synthesis of structurally complex spiroindan-2,2'-pyrrolidines 2 and 3 with complete regioselectivity and high stereoselectivity from acyclic precursors.
Cheng
Xin
X
Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Liang
Fushun
F
Shi
Fan
F
Zhang
Lei
L
Liu
Qun
Q
D000081:Acetamides / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000081:Acetamides; D000447:Aldehydes; D001372:Aza Compounds; D007659:Ketones; D011759:Pyrrolidines; D013141:Spiro Compounds