Enantiocontrolled synthesis of spirooxindoles based on the [5 + 2] cycloaddition of a Tp(CO)(2)Mo(pyridinyl) scaffold (Tp = hydridotrispyrazolylborate).
[structure] A [5 + 2] cycloaddition of the pyridinyl pi-complex (-)-1 (98% ee) to methyleneoxindole 2 afforded the spirooxindole complex (-)-3 in high enantiomeric purity. Complex (-)-3 was converted to pyrrolidine (-)-8 (97% ee), which is related to potent cytotoxic analogues of the spirotryprostatins alkaloids.
Malinakova
H C
HC
Sanford S. Atwood Chemistry Center, Emory University, 1515 Pierce Drive, Atlanta, Georgia, 30322, USA.
Liebeskind
L S
LS
D000470:Alkaloids / Q000138:chemical synthesis*; D001881:Borates / Q000737:chemistry*; D003500:Cyclization; D006868:Hydrolysis; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D009942:Organometallic Compounds / Q000737:chemistry*; D010126:Ozone; D011759:Pyrrolidines / Q000138:chemical synthesis; D013237:Stereoisomerism
D000470:Alkaloids; D001881:Borates; D007202:Indicators and Reagents; D007211:Indoles; D009942:Organometallic Compounds; D011759:Pyrrolidines; C419464:hydridotrispyrazolylborate-(CO)2Mo(pyridinyl); D010126:Ozone