Superacid-Promoted Reactions of N-Acyliminium Ions: An Effective Route to Substituted 3-Oxo-1,2,3,4-tetrahydroisoquinolines and Related Products

ABSTRACT Intramolecular cyclizations involving N-acyliminium ions are shown to give products in good yields from reactions with CF 3 SO 3 H (triflic acid). The resulting 3-oxo-1,2,3,4-tetrahydroisoquinolines have been converted in high yields to 1,2-diaryl-1,2,3,4-tetrahydroisoquinolines, which have...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2006-06, Vol.2006 (11), p.1775-1780
Main Authors: Zhang, Yiliang, Kindelin, Patrick J., DeSchepper, Daniel J., Zheng, Chong, Klumpp, Douglas A.
Format: Article
Language:English
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Summary:ABSTRACT Intramolecular cyclizations involving N-acyliminium ions are shown to give products in good yields from reactions with CF 3 SO 3 H (triflic acid). The resulting 3-oxo-1,2,3,4-tetrahydroisoquinolines have been converted in high yields to 1,2-diaryl-1,2,3,4-tetrahydroisoquinolines, which have been recently shown to be selective estrogen receptor modulators. In a reaction using a chiral N-acyliminium ion, cyclization is found to occur in moderately high diastereoselectivity. Several examples of intermolecular triflic acid-promoted reactions are also reported.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-942387