851010-71-4Relevant articles and documents
Asymmetric [3+2] Annulations to Construct 1,2-Bispirooxindoles Incorporating a Dihydropyrrolidine Motif
He, Qing,Du, Wei,Chen, Ying-Chun
, p. 3782 - 3791 (2017)
Constructing chiral bispirooxindoles is difficult to achieve but highly attractive owing to their many potential applications in medicinal chemistry. Here we present an asymmetric [3+2] annulation reaction of Morita–Baylis–Hillman carbonates from isatins and isatin-based N-Boc-ketimines under the catalysis of a newly designed multifunctional 4-dimethylaminopyridine-type substance. The reaction shows high γ-regioselectivity, producing highly complex 1,2-bispirooxindoles incorporating a dihydropyrrolidine motif in excellent yields with moderate to outstanding stereoselectivity (dr>19:1, up to >99% ee). This protocol has been expanded to utilize trifluoromethyl-containing ketimines, delivering complicated architectures with fused and spirocyclic frameworks in modest enantioselectivity. (Figure presented.).
Kinetic resolution of sec-alcohols using a new class of readily assembled (S)-proline-derived 4-(pyrrolidino)-pyridine analogues
Dalaigh, Ciaran O.,Hynes, Stephen J.,Maher, Declan J.,Connon, Stephen J.
, p. 981 - 984 (2007/10/03)
We report the development of a new class of readily prepared chiral 4-(pyrrolidino)-pyridine catalysts capable of exploiting both van der Waals (π) and H-bonding interactions, thus allowing remote chiral information to stereo-chemically control the kinetic resolution of sec-alcohols. The Royal Society of Chemistry 2005.
