- Abstract:
- A direct enantio- and diastereoselective N-acyliminium cyclization cascade through chiral phosphoric acid catalyzed condensation of tryptamines with γ- and δ-ketoacid derivatives to provide architecturally complex heterocycles has been developed. The reaction is technically simple to perform, atom-efficient, and broad in scope. Employing 10 mol % of (R)-BINOL derived chiral phosphoric acids in refluxing toluene allowed the polycyclic product materials to be generated in good yields (53-99%) and moderate to high enantioselectivities (68-98% ee).
- Publication status:
- Published
- Publisher copy:
- 10.1021/ol101651t
-
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- Journal:
- Organic letters
- Volume:
- 12
- Issue:
- 21
- Pages:
- 4720-4723
- Publication date:
- 2010-11-05
- DOI:
- EISSN:
-
1523-7052
- ISSN:
-
1523-7060
- URN:
-
uuid:7b88a90a-041d-4c5d-922b-4c6e1ac5851a
- Source identifiers:
-
90279
- Local pid:
- pubs:90279
- Language:
- English
- Keywords:
- Copyright date:
- 2010
Journal article
Direct enantioselective Bronsted acid catalyzed N-acyliminium cyclization cascades of tryptamines and ketoacids.
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