ChemInform Abstract: Engaging Allene-Derived Zwitterions in an Unprecedented Mode of Asymmetric [3 + 2]-Annulation Reaction

Autor: Miguel Garcia‐Castro, Muthukumar G. Sankar, Kamal Kumar, Carsten Strohmann, Christopher Golz
Rok vydání: 2016
Předmět:
Zdroj: ChemInform. 47
ISSN: 0931-7597
DOI: 10.1002/chin.201650081
Popis: Catalytic addition of chiral phosphine, that is, (R)- or (S)-SITCP, to an α-substituted allene ester generated a zwitterionic dipole. Under optimized reaction conditions, this dipole could engage isatine-derived N-Boc-ketimines in a novel mode of [3+2] annulation reaction. Pyrrolinyl spirooxindoles are thus afforded in high yields and with excellent enantioselectivities. The unprecedented annulation reaction successfully facilitated the construction of sp(3) -rich and highly substituted 3,2'-pyrrolidinyl spirooxindoles supporting many chiral centers.
Databáze: OpenAIRE