Ring-closing metathesis strategy to P-heterocycles

Hanson, Paul R.; Stoianova, Diana S.

doi:10.1016/s0040-4039(99)00479-7

Cited by 48 publications

(23 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[112][113][114] Ac ouple of years later,r eports on the synthesis of oxaphospholenes through RCM were appearing. [115,116] Symmetrical phosphornates were cyclized with the first generation Grubbs catalyst, although in low yields, with high catalyst loadings, reflux conditions and long reaction times (Scheme 30, conditions A). [115,117] Moreover,t he catalyst provedt ob en ot very selective, resulting in the formation of mixtureso f5-a nd 7-membered cycles.…”

Section: Throughring-closingmetathesismentioning

confidence: 99%

“…[115,116] Symmetrical phosphornates were cyclized with the first generation Grubbs catalyst, although in low yields, with high catalyst loadings, reflux conditions and long reaction times (Scheme 30, conditions A). [115,117] Moreover,t he catalyst provedt ob en ot very selective, resulting in the formation of mixtureso f5-a nd 7-membered cycles. In 2000, Timmer demonstratedt he superiority of the second generation Grubbs catalyst, synthesizingo xaphos-Scheme28.…”

Section: Throughring-closingmetathesismentioning

confidence: 99%

See 1 more Smart Citation

Fifty Years of (Benz)oxaphospholene Chemistry

Berton

Heugebaert

Virieux

et al. 2017

Chemistry A European J

View full text Add to dashboard Cite

The first synthesis of benzoxaphospholenes dates back to the 1960s. Since then,t he structuralv ariety of reported (benz)oxaphospholenesh as steadily increased. Organophosphorusc ompounds have caught the interesto fs ynthetic chemists for ac ouple of decades now because of their interesting biological properties. Oxaphospholenes,i n particular,c ould serve as carbohydrate mimetics, and benzoxaphospholenes have been reported to possess bactericidal, insecticidal, herbicidal, and fungistatical properties. Transesterification reactions and addition of phosphorus nucleophiles to carbonylc ompoundsw ere reaction types that led to the production of the first (benz)oxaphospholenes.When it was discovered that allenylphosphonates could easily be obtainedf rom propargyl alcohols and dialkylh alophosphites, the electrophile-induced cyclization reaction of these allenylphosphonate precursors resulted in ah uge boom in the amounto fr eports on oxaphospholene synthesis. To this day,t his methodi ss till frequently used. Ring-closing metathesis and Horner-Wadsworth-Emmons reactions have also provent heir potentialf or the preparation of oxaphospholenes. In recent years, Pd, Rh and Au-catalysis have made their entry,g enerating (benz)oxaphospholenes from a wide variety of simple substrates. Ac ouple of miscellaneous methods are summarized at the end of the Review.[a] J.

show abstract

Section: Throughring-closingmetathesismentioning

confidence: 99%

Section: Throughring-closingmetathesismentioning

confidence: 99%

Fifty Years of (Benz)oxaphospholene Chemistry

Berton

Heugebaert

Virieux

et al. 2017

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Hanson and Stoianova were the first to report a preparation of P-heterocycles by RCM of acyclic vinylphosphonates or phosphonamides (Scheme 48) [54].…”

Section: Rcmmentioning

confidence: 99%

Metathesis of heteroatom-substituted olefins and alkynes: Current scope and limitations

Weghe

Bisseret

Blanchard

et al. 2006

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

“…Utilizing RCM, 4 simple 5-, 6- and 7-membered sultam derivatives from the corresponding allyl and vinyl sulfonamides were readily accessed. 5 In the cases of RCM with vinyl sulfonamides, the corresponding sultam retains the α , β -unsaturated functionality incorporated within the cycle for diversification utilizing an aza-Michael protocol.…”

Section: Introductionmentioning

confidence: 99%

Triazole-Containing Isothiazolidine 1,1-Dioxide Library Synthesis: One-Pot, Multi-Component Protocols for Small Molecular Probe Discovery

et al. 2011

Self Cite

View full text Add to dashboard Cite

The construction of two libraries of triazole-containing isothiazolidine 1,1-dioxides is reported utilizing either a one-pot click/aza-Michael or click/OACC esterification protocol. One core dihydroisothiazole 1,1-dioxide scaffold was prepared rapidly on multi-gram scale via RCM and was subjected to a one-pot multi-component click/aza-Michael protocol with an array of amines and azides for the generation of a 180-member triazole-containing isothiazolidine 1,1-dioxide library. Alternatively, three daughter scaffolds were generated via the aza-Michael of three amino alcohols, followed by a one-pot, multi-component click/esterification protocol utilizing a ROMP-derived coupling reagent, oligomeric alkyl carbodiimide (OACC) to generate a 41-member library of triazole-containing isothiazole 1,1-dioxides.

show abstract

Ring-closing metathesis strategy to P-heterocycles

Cited by 48 publications

References 20 publications

Fifty Years of (Benz)oxaphospholene Chemistry

Fifty Years of (Benz)oxaphospholene Chemistry

Metathesis of heteroatom-substituted olefins and alkynes: Current scope and limitations

Triazole-Containing Isothiazolidine 1,1-Dioxide Library Synthesis: One-Pot, Multi-Component Protocols for Small Molecular Probe Discovery

Contact Info

Product

Resources

About