A modular pathway consisting of the reaction triad (sulfonylation - Mitsunobu alkylation � intramolecular SNAr) utilizing a range of substrates to expand the scope, including diols and amino alcohols in conjunction with o-fluorobenzenesulfonamides to access skeletally diverse benzofused and bridged sultams is reported.  Previous work developed in our labs resulted in a reaction pairing strategy employing the aforementioned reaction triad in a sulfonylation�SNAr�Mitsunobu alkylation sequence to generate a diverse collection of bridged and non-bridged benzofused sultams.  We herein report a further extension of this work whereby a simple change in the sequence of the reaction triad, alongside utilization of diols and o-fluorobenzenesulfonamides allows for rapid access to 8-, 9- and 10-membered benzo-oxathiazocine-1,1-dioxides.  A change of the diol building block to others such as N-boc amino alcohols provides nitrogen-enriched benzofused sultams.

Reaction-pairing strategies: A diversity-oriented modular approach to polycyclic fused and bridged sultams

247th National Meeting (2014)

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