Enantioselective 1,3-dipolar cycloaddition reaction between diazoacetates and alpha-substituted acroleins: total synthesis of manzacidin A.
A titanium BINOLate catalyzed asymmetric 1,3-dipolar cycloaddition reaction between alpha-substituted acroleins and alkyl diazoacetates has been developed. With this methodology in hand, chiral 2-pyrazolines containing a quaternary stereogenic center were obtained in high to excellent enantioselectivities (up to 95% ee). The synthetic utility of the optically enriched 2-pyrazoline thus obtained was demonstrated in the short synthesis of manzacidin A.
Kano
Taichi
T
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
Hashimoto
Takuya
T
Maruoka
Keiji
K
D000085:Acetates / Q000737:chemistry*; D000171:Acrolein / Q000031:analogs & derivatives* / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D003500:Cyclization; D003979:Diazonium Compounds / Q000737:chemistry*; D009284:Naphthols / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry
D000085:Acetates; D000470:Alkaloids; C406944:BINOL, naphthol; D003979:Diazonium Compounds; D009284:Naphthols; D011743:Pyrimidines; D011758:Pyrroles; C470325:manzacidin A; D000171:Acrolein; D014025:Titanium