Synthesis of new chiral N-heterocyclic carbenes from naturally occurring podophyllotoxin and their application to asymmetric allylic alkylation |
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| Affiliation: | 1. Dipartimento di Scienze Biomediche, Università di Padova, Via Ugo Bassi 58/b, 35131 Padova, Italy;2. Istituto di Neuroscienze (CNR) Sezione di Padova, c/o Dipartimento di Scienze Biomediche, Via Ugo Bassi, 58/b, 35131 Padova, Italy;3. Sorbonne Universités, UPMC Univ Paris 06, CNRS, Institut Parisien de Chimie Moléculaire (IPCM), 75005 Paris, France;4. PSL Research University, Chimie ParisTech, 11 rue Pierre et Marie Curie, 75005 Paris, France |
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| Abstract: | Chiral N-heterocyclic carbenes (NHC) were synthesized from naturally occurring podophyllotoxin. Their coordination with [(η3-allyl)Pd(Br)]2 afforded (NHC)Pd(allyl)Br complexes, whose structures were unambiguously established by X-ray single crystal analysis. These chiral NHC and NHC-Pd-allyl complexes were found to catalyze the substitution reaction of allylic compounds with high conversions and enantioselectivities (up to 87% ee). |
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