One-pot enyne ring-closing metathesis–Diels–Alder reactions for the synthesis of polycyclic sulfamides

Hill-Cousins, Joseph T.; Salim, Sofia S.; Bakar, Youssef M.; Bellingham, Richard K.; Light, Mark E.; Brown, Richard C. D.

doi:10.1016/j.tet.2014.04.014

Cited by 10 publications

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“…One‐pot transformation through enyne RCM [79,80] ‐Diels‐Alder reaction [81] for the synthesis of a series of bicyclic or tricyclic sulfamides was reported (Scheme 29). [82] Enyne metathesis substrates were conveniently prepared from CSI and sequential treatment of t ‐BuOH followed by N ‐allylaniline or N ‐allylbenzylamine to give unsymmetric N ‐Boc protected sulfamides 29.1 in good yields. Rapid conversion through propargylation, deprotection, and N ‐alkylation yielded sulfamide substrates 29.3 for enyne RCM.…”

Section: Methods To Generate Cyclic Sulfamidementioning

confidence: 99%

Implementation of Diverse Synthetic and Strategic Approaches to Biologically Active Sulfamides

Jun

Xie

2021

ChemistrySelect

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Sulfamide compounds are an important class of motif in various applications in pharmaceutical agents, agriculture, and material science. In this review, various synthetic strategies toward acyclic and cyclic sulfamide compounds utilizing many different methods are described. Herein, efficient and innovative synthetic methods ranging from small molecules to large rings for bioactive compounds, small molecules, and catalyst development are discussed.

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Section: Methods To Generate Cyclic Sulfamidementioning

confidence: 99%

Implementation of Diverse Synthetic and Strategic Approaches to Biologically Active Sulfamides

Jun

Xie

2021

ChemistrySelect

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“…Moreover, recently Leach et al [52] described a fluoroustagged linker for the synthesis of several small-and medium-ring and macrocyclic nitrogen heterocycles using RCM, and Poeylaut-Palena and Mata [53] a new strategy for the generation of b-lactams based on a multidetachable olefin linker. Last year (2014) Hill-Cousins et al [54] described a one-pot enyne RCM-Diels-Alder reaction for the synthesis of polycyclic sulfamides. A recent paper written by Hamad and co-authors [55] (and all references mentioned herein) on solid supported ruthenium complexes for olefin metathesis reactions is moreover recommended as further reading about progress in the field.…”

Section: Introductionmentioning

confidence: 99%

Metathesis Reactions on Solid-Phase: Towards New Synthesis Challenges

Franzén

2016

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Today there are many types of transition-metalcatalyzed carbon-carbon bond-forming reactions. Of these, the olefin metathesis has made possible a wide range of transformations with commercially available and easily handled catalysts. Olefin metathesis is widely considered as one of the most powerful synthetic tool in organic chemistry. During the last 20 years many new catalysts with excellent selectivity and efficiency have been developed, also to be used in solid phase organic chemistry protocols. The understanding of the mechanisms and interactions between the catalyst and substrate has resulted that an increasing number of research groups have employed these reactions in multistep procedures and in the synthesis of active pharmaceutical ingredients and natural products. Although the olefin metathesis reaction still proceeds better in homogeneous phase, some structural modifications of the catalyst and new approaches for immobilization have provided interesting possibilities towards more efficient use also in heterogeneous phase. To celebrate 10 years since the Nobel Prize in Chemistry given to Yves Chauvin, Richard Schrock and Robert Grubbs for the ''development of the metathesis method in organic synthesis'' and to summarize recent results obtained in the field of solid phase metathesis chemistry this short review was written.Keywords Olefin metathesis Á Heterogeneous catalysis Á Solid supported catalyst Á Carbon-carbon bonds BackgroundSolid phase ring-closing metathesis (RCM) was first time applied for the synthesis of seven membered cycloolefins in 1996 by van Maarseveen et al. [1]. This cyclization/cleavage approach proceeded in a moderate 54 % yield, due to intermolecular ''metathetical dimerizations'' at the resin according to the authors. As the catalyst, the well-known and utilized ruthenium carbene complex described by Grubbs and co-authors [2-4] was used. A few years later, this strategy was further utilized for the preparation of unsaturated a-estersubstituted N-heterocycles from solid phase-bound olefinic amino acid derivatives.[5] and for the preparation of b-turn mimetics [6] (Fig. 1). The methodology has more recently been used for the macrocyclization strategies to obtain peptide-peptoid hydrid-molecules [7] On the other hand, the ringopening cross metathesis (ROM) of bicyclic alkenes with terminal aryl alkenes on solid support described in 1997 by Cuny et al. [8] is a excellent example of a highly regioselective reaction, marking the start for the utilization of metathesis reactions on solid phase of this reaction-type. Robert Grubbs and co-authors [9-11] described the same year, that norbornyl monomers polymerize readily at ROM conditions. This gave the starting point also for ring-opening metathesis polymerization (ROMP) that found applications for example in the preparation of terpyridine-based silica supports [12], and norbornene-based resins for applications in organic synthesis and other different immobilized polymers [13,14] (Fig. 2). Towards More Complicated StructuresSeeberger and c...

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