Formal Enantioselective Total Synthesis of Schulzeines A–C via Pd–Catalyzed Intramolecular Asymmetric Allylic Amination

Formal enantioselective total synthesis of schulzeines A–C was accomplished, featuring highly efficient Pd-catalyzed asymmetric allylic amination using novel diphosphonite ligands (BOPs) to provide 1-vinyltetrahydroisoquinoline key intermediates, as well as Ru-catalyzed ring-closing metathesis react...

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Veröffentlicht in:	Journal of organic chemistry 2011-08, Vol.76 (15), p.6240-6249
Hauptverfasser:	Lin, Chi-Feng, Ojima, Iwao
Format:	Artikel
Sprache:	eng
Schlagworte:	Allyl Compounds - chemistry Amination Catalysis Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic Compounds, 3-Ring - chemical synthesis Heterocyclic Compounds, 3-Ring - chemistry Lactams - chemical synthesis Lactams - chemistry Ligands Molecular Structure Organic chemistry Palladium - chemistry Preparations and properties Quinolizidines - chemical synthesis Quinolizidines - chemistry Stereoisomerism Sulfuric Acid Esters - chemical synthesis Sulfuric Acid Esters - chemistry
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Beschreibung
Zusammenfassung:	Formal enantioselective total synthesis of schulzeines A–C was accomplished, featuring highly efficient Pd-catalyzed asymmetric allylic amination using novel diphosphonite ligands (BOPs) to provide 1-vinyltetrahydroisoquinoline key intermediates, as well as Ru-catalyzed ring-closing metathesis reaction to construct the key tricyclic cores in enantiopure form with correct absolute configurations.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo2009615