Practical Preparation of N-(1-Alkynyl)sulfonamides and Their Remote Diastereoselective Addition to Aldehydes via Titanation

Aliphatic and aromatic sulfonamides were alkynylated with 1-bromo-1-alkynes in the catalytic presence of CuI to give N-(1-alkynyl)sulfonamides in good to excellent yields. The acetylene−titanium complexes generated from N-(1-alkynyl)benzosultams underwent diastereoselective addition to aldehydes.

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Bibliographic Details
Published in:Organic letters 2004-03, Vol.6 (5), p.727-729
Main Authors: Hirano, Shuji, Tanaka, Ryoichi, Urabe, Hirokazu, Sato, Fumie
Format: Article
Language:English
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Summary:Aliphatic and aromatic sulfonamides were alkynylated with 1-bromo-1-alkynes in the catalytic presence of CuI to give N-(1-alkynyl)sulfonamides in good to excellent yields. The acetylene−titanium complexes generated from N-(1-alkynyl)benzosultams underwent diastereoselective addition to aldehydes.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol036396b