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Direct enantioselective Bronsted acid catalyzed N-acyliminium cyclization cascades of tryptamines and ketoacids.

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

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Publisher copy:
10.1021/ol101651t

Authors


Holloway, CA More by this author
Muratore, ME More by this author
Storer, RL More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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

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