Combining Ring-Closing Metathesis and Hydroformylation Strategies:  A Novel Approach to Spirocyclic γ-Butyrolactones

Schmidt, Bernd; Costisella, Burkhard; Roggenbuck, Rafael; Westhus, Markus; Wildemann, Holger; Eilbracht, Peter

doi:10.1021/jo0157730

Cited by 21 publications

(5 citation statements)

References 45 publications

(72 reference statements)

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“…Finally, it was investigated whether the problem of incomplete conversion observed under an atmosphere of ethylene could be circumvented by diluting the ethylene atmosphere with an inert gas, thereby reducing the number of unproductive metathesis cycles. Although the overall conversion is slightly better if the experiments are run under 12 bars of ethylene and 30 bars of argon ( Table 2, entries [13][14][15][16], no improvement of the selectivity was observed compared to the previous sets of experiments. Our observations differ somewhat from those recently published by Honda et al who investigated the double RCM of a tetraene structurally related to 6a.…”

Section: Regioselective Double Rcm: Fused Vs Dumbbelltype Bicyclic Smentioning

confidence: 93%

Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size‐Selective Ring‐Closing Metathesis

Schmidt

Nave

2007

Adv Synth Catal

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Enantiomerically pure 1,5-hexadiene-3,4-diol, derived from d-mannitol in a few steps, may serve as a starting material for enantiopure dihydropyrans and dihydrofurans bearing an unsaturated side chain which is amenable for further synthetic transformations. The synthesis relies on a ring sizeselective ring-closing metathesis reaction of a triene. Most likely, a catalyst-directing effect of an allylic hydroxy group is responsible for the selectivity.

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Section: Regioselective Double Rcm: Fused Vs Dumbbelltype Bicyclic Smentioning

confidence: 93%

Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size‐Selective Ring‐Closing Metathesis

Schmidt

Nave

2007

Adv Synth Catal

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“…General. General information concerning experimental techniques and product characterization 14b and details for NOE-spectroscopic measurements have been published previously …”

Section: Methodsmentioning

confidence: 99%

Ring-Closing Olefin Metathesis and Radical Cyclization as Competing Pathways

2004

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“…Selective functionalization of the exocyclic double bond in 24 can be achieved by Rhodium-catalysed nselective hydroformylation [65] under mild conditions. Oxidation of the primarily formed lactol to a spirocyclic lactone 27 was achieved with TPAP/NMO (Scheme 9) [66].…”

Section: Trienes With C1-symmetry (Diastereoselective Rcm)mentioning

confidence: 99%

“…Triene 38 (obtained in >99% ee) is cyclized with [Ru-II] to give, after cleavage of the TMS group, RCM Scheme 9. Selective functionalization of exo-and endocyclic C-C-double bonds in dihydropyrans [59,61,66]. …”

Section: Trienes With C1-symmetry (Diastereoselective Rcm)mentioning

confidence: 99%

"Ring Closing Metathesis of Substrates Containing more than two C-Cdouble Bonds: Rapid Access to Functionalized Heterocycles"

Schmidt¹,

Hermanns

2006

COC

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In most cases where ring closing metathesis is applied to the synthesis of heterocycles, α,ω-dienes are used as precursors. If substrates containing more than two double bonds are subjected to a metathesis reaction, carba-or heterocycles bearing additional exocyclic alkene functionality result, or multiple ring closing processes occur. This offers interesting and potentially very useful synthetic perspectives. On the other hand, selectivity problems need to be addressed as the cyclization of substrates with more than two double bonds available for olefin metathesis may result in constitutional isomers or stereoisomers. This review highlights problems and opportunities evolving from ring closing metathesis of tri-, tetra-, and polyenes as a strategy for the selective synthesis of functionalized heterocycles. The chapter on RCM of trienes is subdivided according to the symmetry of the metathesis precursor. The following two chapters deal with the double or multiple RCM of tetra-or polyenes. These processes are further classified according to the preferred cyclization mode. Finally, the application of cascade or domino metathesis reactions to the synthesis of heterocycles will be discussed. These processes can be classified into those where exclusively C-C-double bonds take part in the metathesis reaction, and those where one or more C-C-triple bonds are involved.

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Combining Ring-Closing Metathesis and Hydroformylation Strategies: A Novel Approach to Spirocyclic γ-Butyrolactones

Cited by 21 publications

References 45 publications

Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size‐Selective Ring‐Closing Metathesis

Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size‐Selective Ring‐Closing Metathesis

Ring-Closing Olefin Metathesis and Radical Cyclization as Competing Pathways

"Ring Closing Metathesis of Substrates Containing more than two C-Cdouble Bonds: Rapid Access to Functionalized Heterocycles"

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