Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 62, Pages 14237-14245Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201903832
Keywords
atropisomerism; bifurcation; density functional calculations; ligand design; Negishi coupling; Pd catalysis
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Funding
- NIGMS NIH HHS [GM, GM] Funding Source: Medline
- Directorate for Computer and Information Science and Engineering [DMR-1720256] Funding Source: Medline
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A stereoselective total synthesis of O,N-dimethylhamatine, an analogue of an axially chiral naphthylisoquinoline natural biaryl product from tropical Ancistrocladus lianas, is reported. The route features a late-stage atropo-diastereoselective biaryl bond formation. Generation of this especially challenging, sterically hindered tetra-ortho-substituted array was achieved by using Nolan's (IPr*NHC)PdCinCl pre-catalyst under mild Negishi coupling conditions. Discussion is offered regarding the selectivity obtained experimentally and predicted from DFT calculations on the key biaryl coupling step that leads to the desired M-diastereomer.
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