Literature DB >> 21899284

A modular reaction pairing approach to the diversity-oriented synthesis of fused- and bridged-polycyclic sultams.

Thiwanka B Samarakoon1, Joanna K Loh, Alan Rolfe, Lisa S Le, Sun Young Yoon, Gerald H Lushington, Paul R Hanson.   

Abstract

A reaction pairing strategy centered on utilization of a reaction triad (sulfonylation, S(N)Ar addition and Mitsunobu alkylation) generating skeletally diverse, tricyclic and bicyclic benzofused sultams is reported. Pairing sulfonylation and S(N)Ar reactions yields bridged, tricyclic and bicyclic benzofused sultams. Application of the Mitsunobu reaction in a sulfonylation-Mitsunobu-S(N)Ar pairing allows access to benzthiazocine-1,1-dioxides, while a simple change in the order of pairing to sulfonylation-S(N)Ar-Mitsunobu affords structurally different, bridged tricyclic benzofused sultams.
© 2011 American Chemical Society

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Year:  2011        PMID： 21899284      PMCID： PMC3271938          DOI： 10.1021/ol201962n

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  38 in total

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5.  Synthesis of spirocyclic β- and γ-sultams by one-pot reductive cyclization of cyanoalkylsulfonyl fluorides.

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6.  Exploring chemical diversity via a modular reaction pairing strategy.

Authors:  Joanna K Loh; Sun Young Yoon; Thiwanka B Samarakoon; Alan Rolfe; Patrick Porubsky; Benjamin Neuenswander; Gerald H Lushington; Paul R Hanson
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7.  Application of Silica-Supported Alkylating Reagents in a One-Pot, Sequential Protocol to Diverse Benzoxathiazepine 1,1-Dioxides.

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  8 in total

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