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Gold-Catalyzed Asymmetric Intramolecular Cyclization of N-Allenamides for the Synthesis of Chiral Tetrahydrocarbolines
- Source :
- Angewandte Chemie International Edition. 56:15905-15909
- Publication Year :
- 2017
- Publisher :
- Wiley, 2017.
-
Abstract
- Highly enantioselective gold-catalyzed intramolecular cyclization of N-allenamides was implemented by utilizing a designed chiral sulfinamide phosphine ligand (PC-Phos). This represents the first example of highly enantioselective intramolecular cyclization of N-allenamides. The practicality of this reaction was validated in the total synthesis of (R)-desbromoarborescidine A and formal synthesis of (R)-desbromoarborescidine C and (R)-deplancheine. Moreover, the catalyst system PC-Phos/AuNTf2 proved to be specifically efficient to promote the desymmetrization of N-allenamides in excellent yields with satisfactory ee values.
- Subjects :
- 010405 organic chemistry
Ligand
Stereochemistry
Intramolecular cyclization
Enantioselective synthesis
Total synthesis
General Medicine
General Chemistry
010402 general chemistry
01 natural sciences
Desymmetrization
Catalysis
0104 chemical sciences
chemistry.chemical_compound
Sulfinamide
chemistry
Phosphine
Subjects
Details
- ISSN :
- 14337851
- Volume :
- 56
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie International Edition
- Accession number :
- edsair.doi.dedup.....b4a9d1008aff67c7f1cfcb120ac6745e