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Synfacts 2010(6): 0632-0632  
DOI: 10.1055/s-0029-1219872
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Benzosultams from Cyclic Sulfamidates

Contributor(s): Victor Snieckus, Emilie David
M. Lorion, V. Agouridas, A. Couture*, E. Deniau, P. Grandclaudon
Université Lille Nord de France, Université des Sciences et Technologies de Lille and CNRS, Villeneuve d’Ascq, France
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Publication History

Publication Date:
20 May 2010 (online)

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Significance

Whereas cyclic sulfamidates 1 are easily opened by selective nucleophilic attack at the O-bearing carbon center (A. Avenoza and co-workers Chem. Eur. J. 2009, 15, 9810), the present report demonstrates an intramolecular S(O)2-O bond cleavage by an aryllithiated species on an adjacent benzylic cyclic sulfamidate. After varying a number of parameters, treatment of a degassed solution of 1 and TMEDA with n-BuLi led to the formation of the hydroxylalkyl-chain-tethered benzosultams 2 in good to excellent yields.